EP1662877B1 - 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests - Google Patents
6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests Download PDFInfo
- Publication number
- EP1662877B1 EP1662877B1 EP04765059.3A EP04765059A EP1662877B1 EP 1662877 B1 EP1662877 B1 EP 1662877B1 EP 04765059 A EP04765059 A EP 04765059A EP 1662877 B1 EP1662877 B1 EP 1662877B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- tert
- chf
- cyclohexyl
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 241000607479 Yersinia pestis Species 0.000 title claims description 40
- 241001465754 Metazoa Species 0.000 title claims description 34
- 150000003230 pyrimidines Chemical class 0.000 title description 7
- -1 area Substances 0.000 claims description 529
- 150000001875 compounds Chemical class 0.000 claims description 94
- 239000000460 chlorine Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical group 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 230000000361 pesticidal effect Effects 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 206010061217 Infestation Diseases 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000009395 breeding Methods 0.000 claims description 3
- 230000001488 breeding effect Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 383
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 262
- 239000003921 oil Substances 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 27
- 239000002904 solvent Substances 0.000 description 23
- WPTDJONGJVFDDP-UHFFFAOYSA-N 6-chloro-[1,2,4]triazolo[1,5-a]pyrimidine Chemical class C1=C(Cl)C=NC2=NC=NN21 WPTDJONGJVFDDP-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 21
- 238000012360 testing method Methods 0.000 description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 241000238631 Hexapoda Species 0.000 description 16
- 241000239223 Arachnida Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 241000132121 Acaridae Species 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- 239000006072 paste Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- 241001600408 Aphis gossypii Species 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 241000721621 Myzus persicae Species 0.000 description 5
- 241001556089 Nilaparvata lugens Species 0.000 description 5
- 241000176086 Sogatella furcifera Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 241001425390 Aphis fabae Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 241001521235 Spodoptera eridania Species 0.000 description 3
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 2
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZDOOQPFIGYHZFV-UHFFFAOYSA-N 2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1C(CC)OCC1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-UHFFFAOYSA-N 0.000 description 2
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical compound NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- BGNLXETYTAAURD-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-amine Chemical compound CC(C)(C)C1CCC(N)CC1 BGNLXETYTAAURD-UHFFFAOYSA-N 0.000 description 2
- MHIRKGQXSLWNPS-UHFFFAOYSA-N 6,7-dichloro-5-ethyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=C(Cl)C(CC)=NC2=NC=NN21 MHIRKGQXSLWNPS-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001166626 Aulacorthum solani Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000045232 Canavalia ensiformis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000191839 Chrysomya Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001581006 Dysaphis plantaginea Species 0.000 description 2
- 239000005898 Fenoxycarb Substances 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 239000005907 Indoxacarb Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 241000512856 Myzus ascalonicus Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001402070 Sappaphis piri Species 0.000 description 2
- 241000180219 Sitobion avenae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 125000005544 phthalimido group Chemical group 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- QGCLEUGNYRXBMZ-LURJTMIESA-N (1s)-1-(4-fluorophenyl)ethanamine Chemical compound C[C@H](N)C1=CC=C(F)C=C1 QGCLEUGNYRXBMZ-LURJTMIESA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- 125000006112 1, 1-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006120 1,1,2-trimethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006150 1,1,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004884 1,1,2-trimethylpropylcarbonyl group Chemical group CC(C(C)C)(C(=O)*)C 0.000 description 1
- 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006142 1,1-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004876 1,1-dimethylbutylcarbonyl group Chemical group CC(CCC)(C(=O)*)C 0.000 description 1
- 125000006098 1,1-dimethylethyl sulfinyl group Chemical group 0.000 description 1
- 125000004866 1,1-dimethylethylcarbonyl group Chemical group CC(C)(C(=O)*)C 0.000 description 1
- 125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 1
- 125000006103 1,1-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006133 1,1-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004867 1,1-dimethylpropylcarbonyl group Chemical group CC(CC)(C(=O)*)C 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000006121 1,2,2-trimethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006151 1,2,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004885 1,2,2-trimethylpropylcarbonyl group Chemical group CC(C(C)(C)C)C(=O)* 0.000 description 1
- 125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006113 1,2-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006143 1,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004877 1,2-dimethylbutylcarbonyl group Chemical group CC(C(CC)C)C(=O)* 0.000 description 1
- 125000006104 1,2-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006134 1,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004868 1,2-dimethylpropylcarbonyl group Chemical group CC(C(C)C)C(=O)* 0.000 description 1
- 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006114 1,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006144 1,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004878 1,3-dimethylbutylcarbonyl group Chemical group CC(CC(C)C)C(=O)* 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000006073 1-ethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006122 1-ethyl-1-methylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006152 1-ethyl-1-methylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004886 1-ethyl-1-methylpropylcarbonyl group Chemical group C(C)C(CC)(C(=O)*)C 0.000 description 1
- 125000006036 1-ethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006081 1-ethyl-2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006123 1-ethyl-2-methylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006153 1-ethyl-2-methylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004887 1-ethyl-2-methylpropylcarbonyl group Chemical group C(C)C(C(C)C)C(=O)* 0.000 description 1
- 125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006118 1-ethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006148 1-ethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004882 1-ethylbutylcarbonyl group Chemical group C(C)C(CCC)C(=O)* 0.000 description 1
- 125000006106 1-ethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006136 1-ethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004870 1-ethylpropylcarbonyl group Chemical group C(C)C(CC)C(=O)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006044 1-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006100 1-methylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006130 1-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004679 1-methylbutylcarbonyl group Chemical group CC(CCC)C(=O)* 0.000 description 1
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
- 125000006094 1-methylethyl sulfinyl group Chemical group 0.000 description 1
- 125000004677 1-methylethylcarbonyl group Chemical group CC(C)C(=O)* 0.000 description 1
- 125000006108 1-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000006138 1-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000004872 1-methylpentylcarbonyl group Chemical group CC(CCCC)C(=O)* 0.000 description 1
- 125000006096 1-methylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006127 1-methylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004678 1-methylpropylcarbonyl group Chemical group CC(CC)C(=O)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
- 125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006115 2,2-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006145 2,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004879 2,2-dimethylbutylcarbonyl group Chemical group CC(CC(=O)*)(CC)C 0.000 description 1
- 125000006105 2,2-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006135 2,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 0.000 description 1
- 125000006068 2,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006116 2,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006146 2,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004880 2,3-dimethylbutylcarbonyl group Chemical group CC(CC(=O)*)C(C)C 0.000 description 1
- HHLGARPFXWIYTE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanamine Chemical compound NCCC1=CC=C(OC(F)(F)F)C=C1 HHLGARPFXWIYTE-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
- 125000006076 2-ethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006077 2-ethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006119 2-ethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006149 2-ethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004883 2-ethylbutylcarbonyl group Chemical group C(C)C(CC(=O)*)CC 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006045 2-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000006101 2-methylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006131 2-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004680 2-methylbutylcarbonyl group Chemical group CC(CC(=O)*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006109 2-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000006139 2-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000004873 2-methylpentylcarbonyl group Chemical group CC(CC(=O)*)CCC 0.000 description 1
- 125000006097 2-methylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000006071 3,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006072 3,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006117 3,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006147 3,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004881 3,3-dimethylbutylcarbonyl group Chemical group CC(CCC(=O)*)(C)C 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006046 3-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006102 3-methylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006132 3-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004681 3-methylbutylcarbonyl group Chemical group CC(CCC(=O)*)C 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006110 3-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000006140 3-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000004874 3-methylpentylcarbonyl group Chemical group CC(CCC(=O)*)CC 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006047 4-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006111 4-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000006141 4-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000004875 4-methylpentylcarbonyl group Chemical group CC(CCCC(=O)*)C 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- QCSQQMXJXKLRJV-UHFFFAOYSA-N 6,7-dichloro-5-(1-fluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=C(Cl)C(C(F)C)=NC2=NC=NN21 QCSQQMXJXKLRJV-UHFFFAOYSA-N 0.000 description 1
- WEBSNJZIXOEXTM-UHFFFAOYSA-N 6,7-dichloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=C(Cl)C(C)=NC2=NC=NN21 WEBSNJZIXOEXTM-UHFFFAOYSA-N 0.000 description 1
- XXKQOHBZZCXEQE-QMMMGPOBSA-N 6-chloro-n-[(1s)-1-(4-fluorophenyl)ethyl]-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1([C@@H](NC=2N3N=CN=C3N=C(C)C=2Cl)C)=CC=C(F)C=C1 XXKQOHBZZCXEQE-QMMMGPOBSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 239000005651 Acequinocyl Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241001014341 Acrosternum hilare Species 0.000 description 1
- 241001506414 Aculus Species 0.000 description 1
- 241000253988 Acyrthosiphon Species 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000917225 Adelges laricis Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256176 Aedes vexans Species 0.000 description 1
- 241001470785 Agrilus sinuatus Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241001031864 Agriotes obscurus Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241001652650 Agrotis subterranea Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241000238682 Amblyomma americanum Species 0.000 description 1
- 241001480834 Amblyomma variegatum Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241001136525 Anastrepha ludens Species 0.000 description 1
- 241001256085 Anisandrus dispar Species 0.000 description 1
- 241000132163 Anopheles maculipennis Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001156002 Anthonomus pomorum Species 0.000 description 1
- 241000625764 Anticarsia gemmatalis Species 0.000 description 1
- 241000566651 Aphis forbesi Species 0.000 description 1
- 241000726841 Aphis grossulariae Species 0.000 description 1
- 241000569145 Aphis nasturtii Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241000496365 Aphis sambuci Species 0.000 description 1
- 241000726735 Aphis schneideri Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 241001480752 Argas persicus Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- 241001340598 Argyresthia conjugella Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241001503477 Athalia rosae Species 0.000 description 1
- 241001174347 Atomaria Species 0.000 description 1
- 241000726102 Atta cephalotes Species 0.000 description 1
- 241000908426 Atta sexdens Species 0.000 description 1
- 241000580299 Atta texana Species 0.000 description 1
- 241001367053 Autographa gamma Species 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- 241001490249 Bactrocera oleae Species 0.000 description 1
- 241001302798 Bemisia argentifolii Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000005653 Bifenazate Substances 0.000 description 1
- 239000005874 Bifenthrin Substances 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001629132 Blissus leucopterus Species 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 241000273318 Brachycaudus cardui Species 0.000 description 1
- 241000310266 Brachycaudus helichrysi Species 0.000 description 1
- 241000272639 Brachycaudus mimeuri Species 0.000 description 1
- 241000256548 Brachycaudus prunicola Species 0.000 description 1
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- 241000982105 Brevicoryne brassicae Species 0.000 description 1
- 241001643371 Brevipalpus phoenicis Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241001414203 Bruchus lentis Species 0.000 description 1
- 241001414201 Bruchus pisorum Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 241001491790 Bupalus piniaria Species 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000259719 Byctiscus betulae Species 0.000 description 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 1
- 241000776777 Cacopsylla mali Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001094772 Capitophorus Species 0.000 description 1
- 241001350371 Capua Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001130355 Cassida nebulosa Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241001098608 Ceratophyllus Species 0.000 description 1
- 241001124201 Cerotoma trifurcata Species 0.000 description 1
- 241001087583 Chaetocnema tibialis Species 0.000 description 1
- 241001094931 Chaetosiphon fragaefolii Species 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000255942 Choristoneura fumiferana Species 0.000 description 1
- 241001525905 Choristoneura murinana Species 0.000 description 1
- 241001124564 Choristoneura occidentalis Species 0.000 description 1
- 241001367803 Chrysodeixis includens Species 0.000 description 1
- 241000983417 Chrysomya bezziana Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RNIDGCURSLWKTK-YOGCLGLASA-N ClC=1C(C(F)C)=NC2=NC=NN2C=1N[C@H]1CC[C@@H](C(C)(C)C)CC1 Chemical compound ClC=1C(C(F)C)=NC2=NC=NN2C=1N[C@H]1CC[C@@H](C(C)(C)C)CC1 RNIDGCURSLWKTK-YOGCLGLASA-N 0.000 description 1
- GCGSUBYUAVJUML-TXEJJXNPSA-N ClC=1C(CC)=NC2=NC=NN2C=1N[C@H]1CC[C@@H](C(C)(C)C)CC1 Chemical compound ClC=1C(CC)=NC2=NC=NN2C=1N[C@H]1CC[C@@H](C(C)(C)C)CC1 GCGSUBYUAVJUML-TXEJJXNPSA-N 0.000 description 1
- 241000683561 Conoderus Species 0.000 description 1
- 241001663470 Contarinia <gall midge> Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000304165 Cordylobia anthropophaga Species 0.000 description 1
- 241000902369 Crioceris asparagi Species 0.000 description 1
- 241001094916 Cryptomyzus ribis Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005891 Cyromazine Substances 0.000 description 1
- 241001090151 Cyrtopeltis Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000969022 Dasineura Species 0.000 description 1
- 241000084475 Delia antiqua Species 0.000 description 1
- 241001585354 Delia coarctata Species 0.000 description 1
- 241001414892 Delia radicum Species 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 241001631712 Dendrolimus pini Species 0.000 description 1
- 241000119571 Dermacentor silvarum Species 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000916723 Diabrotica longicornis Species 0.000 description 1
- 241000489977 Diabrotica virgifera Species 0.000 description 1
- 241001012951 Diaphania nitidalis Species 0.000 description 1
- 241000879145 Diatraea grandiosella Species 0.000 description 1
- 241000508744 Dichromothrips Species 0.000 description 1
- 241001480349 Diestrammena asynamora Species 0.000 description 1
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001080889 Dociostaurus maroccanus Species 0.000 description 1
- 241001274799 Dreyfusia nordmannianae Species 0.000 description 1
- 241001274798 Dreyfusia piceae Species 0.000 description 1
- 241001088941 Dysaphis radicola Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000353522 Earias insulana Species 0.000 description 1
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 1
- 241000400698 Elasmopalpus lignosellus Species 0.000 description 1
- 239000005894 Emamectin Substances 0.000 description 1
- 241000995027 Empoasca fabae Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 241001183322 Epitrix hirtipennis Species 0.000 description 1
- 241001491690 Erannis defoliaria Species 0.000 description 1
- 241001558857 Eriophyes Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- 239000005895 Esfenvalerate Substances 0.000 description 1
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241000515837 Eurygaster integriceps Species 0.000 description 1
- 241000098297 Euschistus Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 239000005656 Fenazaquin Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005899 Fipronil Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000005948 Formetanate Substances 0.000 description 1
- 241000654868 Frankliniella fusca Species 0.000 description 1
- 241000927584 Frankliniella occidentalis Species 0.000 description 1
- 241000189591 Frankliniella tritici Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001660201 Gasterophilus intestinalis Species 0.000 description 1
- 241000257323 Glossina morsitans Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241001232715 Granaria Species 0.000 description 1
- 241000659076 Grapholitha Species 0.000 description 1
- 241000659001 Grapholitha molesta Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241000241125 Gryllotalpa gryllotalpa Species 0.000 description 1
- 241000257232 Haematobia irritans Species 0.000 description 1
- 241001147381 Helicoverpa armigera Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241001581044 Hellula undalis Species 0.000 description 1
- 241001466007 Heteroptera Species 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 241000291719 Hoplocampa minuta Species 0.000 description 1
- 241000291732 Hoplocampa testudinea Species 0.000 description 1
- 241001251778 Hyalomma truncatum Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241001153231 Hylobius abietis Species 0.000 description 1
- 241000370523 Hypena scabra Species 0.000 description 1
- 241001508570 Hypera brunneipennis Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 241000310291 Hyperomyzus lactucae Species 0.000 description 1
- 241001531327 Hyphantria cunea Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 241000546120 Ips typographus Species 0.000 description 1
- 241001480843 Ixodes ricinus Species 0.000 description 1
- 241000472347 Ixodes rubicundus Species 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241001300668 Jatropha integerrima Species 0.000 description 1
- 241000400431 Keiferia lycopersicella Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001658023 Lambdina fiscellaria Species 0.000 description 1
- 241001142635 Lema Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000560153 Leptoglossus phyllopus Species 0.000 description 1
- 241000540210 Leucoptera coffeella Species 0.000 description 1
- 241001578972 Leucoptera malifoliella Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000673175 Limonius californicus Species 0.000 description 1
- 241000594031 Liriomyza sativae Species 0.000 description 1
- 241001520143 Liriomyza trifolii Species 0.000 description 1
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001261104 Lobesia botrana Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000193981 Loxostege sticticalis Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241000736227 Lucilia sericata Species 0.000 description 1
- 239000005912 Lufenuron Substances 0.000 description 1
- 241000501345 Lygus lineolaris Species 0.000 description 1
- 241001492180 Lygus pratensis Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241001314285 Lymantria monacha Species 0.000 description 1
- 241001581015 Lyonetia clerkella Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000180172 Macrosiphum rosae Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241001422926 Mayetiola hordei Species 0.000 description 1
- 241000171293 Megoura viciae Species 0.000 description 1
- 241000726778 Melanaphis Species 0.000 description 1
- 241001478935 Melanoplus bivittatus Species 0.000 description 1
- 241001478965 Melanoplus femurrubrum Species 0.000 description 1
- 241001582344 Melanoplus mexicanus Species 0.000 description 1
- 241000922538 Melanoplus sanguinipes Species 0.000 description 1
- 241001051646 Melanoplus spretus Species 0.000 description 1
- 241001394950 Melanotus communis (Gyllenhal, 1817) Species 0.000 description 1
- 241000828959 Melolontha hippocastani Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 239000005951 Methiocarb Substances 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- 239000005917 Methoxyfenozide Substances 0.000 description 1
- 241000168713 Metopolophium dirhodum Species 0.000 description 1
- 241000952627 Monomorium pharaonis Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000581981 Muscina stabulans Species 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 241000332345 Myzus cerasi Species 0.000 description 1
- 241000332347 Myzus varians Species 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241000133263 Nasonovia ribisnigri Species 0.000 description 1
- 241001671709 Nezara viridula Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000916006 Nomadacris septemfasciata Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000488557 Oligonychus Species 0.000 description 1
- 241000219830 Onobrychis Species 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241001465803 Orgyia pseudotsugata Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000975417 Oscinella frit Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241001480756 Otobius megnini Species 0.000 description 1
- 241001160353 Oulema melanopus Species 0.000 description 1
- 241001570894 Oulema oryzae Species 0.000 description 1
- 241000604373 Ovatus Species 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 241000486438 Panolis flammea Species 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000721451 Pectinophora gossypiella Species 0.000 description 1
- 241000562493 Pegomya Species 0.000 description 1
- 241000609952 Pemphigus bursarius Species 0.000 description 1
- 241001013804 Peridroma saucia Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001253326 Perkinsiella saccharicida Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241001579681 Phalera bucephala Species 0.000 description 1
- 241001401861 Phorodon humuli Species 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 241001439019 Phthorimaea operculella Species 0.000 description 1
- 241001525654 Phyllocnistis citrella Species 0.000 description 1
- 241001517955 Phyllonorycter blancardella Species 0.000 description 1
- 241001227717 Phyllopertha horticola Species 0.000 description 1
- 241001640279 Phyllophaga Species 0.000 description 1
- 241000275067 Phyllotreta Species 0.000 description 1
- 241000517946 Phyllotreta nemorum Species 0.000 description 1
- 241000437063 Phyllotreta striolata Species 0.000 description 1
- 241001396980 Phytonemus pallidus Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 239000005924 Pirimiphos-methyl Substances 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000254101 Popillia japonica Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 239000005925 Pymetrozine Substances 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241000590363 Reticulitermes lucifugus Species 0.000 description 1
- 241000157279 Rhagoletis cerasi Species 0.000 description 1
- 241001136903 Rhagoletis pomonella Species 0.000 description 1
- 241001480837 Rhipicephalus annulatus Species 0.000 description 1
- 241001481704 Rhipicephalus appendiculatus Species 0.000 description 1
- 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
- 241000864202 Rhipicephalus evertsi Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241000426569 Rhopalosiphum insertum Species 0.000 description 1
- 241000167882 Rhopalosiphum maidis Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 241001575051 Rhyacionia Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000509418 Sarcoptidae Species 0.000 description 1
- 241000254026 Schistocerca Species 0.000 description 1
- 241000254030 Schistocerca americana Species 0.000 description 1
- 241000722027 Schizaphis graminum Species 0.000 description 1
- 241000343234 Scirtothrips citri Species 0.000 description 1
- 241001168723 Sitona lineatus Species 0.000 description 1
- 241000254181 Sitophilus Species 0.000 description 1
- 241000753145 Sitotroga cerealella Species 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241000736128 Solenopsis invicta Species 0.000 description 1
- 241000277984 Sparganothis pilleriana Species 0.000 description 1
- 239000005930 Spinosad Substances 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001161749 Stenchaetothrips biformis Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000916145 Tarsonemidae Species 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005938 Teflubenzuron Substances 0.000 description 1
- 239000005939 Tefluthrin Substances 0.000 description 1
- 241000488607 Tenuipalpidae Species 0.000 description 1
- 241000897276 Termes Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 241000488530 Tetranychus pacificus Species 0.000 description 1
- 241001231950 Thaumetopoea pityocampa Species 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 241000051707 Thyanta perditor Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241001240492 Tipula oleracea Species 0.000 description 1
- 241000511627 Tipula paludosa Species 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000271862 Toxoptera Species 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 239000005942 Triflumuron Substances 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 241001389006 Tuta absoluta Species 0.000 description 1
- 241001274787 Viteus Species 0.000 description 1
- 241000353224 Xenopsylla Species 0.000 description 1
- 241001466330 Yponomeuta malinellus Species 0.000 description 1
- 241000495395 Zeiraphera canadensis Species 0.000 description 1
- 241001136529 Zeugodacus cucurbitae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 1
- MYPKGPZHHQEODQ-UHFFFAOYSA-N [3-(dimethylaminomethylideneamino)phenoxy]carbonyl-methylazanium;chloride Chemical compound Cl.CNC(=O)OC1=CC=CC(N=CN(C)C)=C1 MYPKGPZHHQEODQ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical group C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- GMAUQNJOSOMMHI-JXAWBTAJSA-N alanycarb Chemical compound CSC(\C)=N/OC(=O)N(C)SN(CCC(=O)OCC)CC1=CC=CC=C1 GMAUQNJOSOMMHI-JXAWBTAJSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 description 1
- 229950000775 cyromazine Drugs 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- VEENJGZXVHKXNB-VOTSOKGWSA-N dicrotophos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)N(C)C VEENJGZXVHKXNB-VOTSOKGWSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 125000005072 dihydrothiopyranyl group Chemical group S1C(CCC=C1)* 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 1
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 description 1
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 1
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- RMFNNCGOSPBBAD-MDWZMJQESA-N formetanate Chemical compound CNC(=O)OC1=CC=CC(\N=C\N(C)C)=C1 RMFNNCGOSPBBAD-MDWZMJQESA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- HAWJXYBZNNRMNO-UHFFFAOYSA-N furathiocarb Chemical compound CCCCOC(=O)N(C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 HAWJXYBZNNRMNO-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229910001751 gemstone Inorganic materials 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000006107 n-hexyl sulfinyl group Chemical group 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- 125000006099 n-pentyl sulfinyl group Chemical group 0.000 description 1
- 125000006129 n-pentyl sulfonyl group Chemical group 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical compound CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229960004623 paraoxon Drugs 0.000 description 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- the present invention relates to 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests.
- WO 03/039259 describes substituted s-1,2,4-triazolo[1,5-a]pyrimidine compounds having fungicidal activity.
- WO 02/50077 discloses insecticidal and fungicidal 6-aryl/heterocycle-7-amine-[1,2,4]-triazolo[1,5a]-pyrimidines and US 4,144,330 discloses insecticidal and acaricidal 5,7-dimethyl- [1,2,4]-triazolo[1,5a]-pyrimidine phosphoric acid derivatives.
- the 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I as defined herein and the agriculturally acceptable salts thereof are particularly useful for combating animal pests which are harmful to crops. Therefore the present invention also relates to the use of the compounds of the general formula I for protecting crops from attack or infestation by animal pests.
- the present invention provides a method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of a 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I and/or at least one salt thereof.
- the invention also relates to 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidine compounds of the general formula (I)' wherein R 1 , R 2 and R 4 are as defined as in claim 17 ; and to the agriculturally useful salts thereof.
- the invention relates to agricultural compositions, preferably in the form of directly sprayable solutions, emulsions, pastes oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprise at least one 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidine of the general formula (I)' as defined above, admixed with one or more agronomically acceptable inert, solid or liquid carrier(s) and, if desired, at least one surfactant.
- Salts of the compounds of the formula I which are suitable for the use according to the invention are especially agriculturally acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question.
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae la and Ib with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
- the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
- the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
- halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
- C 1 -C 6 -alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfur refers, for example, to methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl, 1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl,
- the heteroatom can be arranged in the alkylene chain at any position or at the end of the chain so that it connects the alkylene chain to the radical R 4a .
- the heteroatom is not arranged at the end of the alkylene chain.
- the heteroatom is preferably oxygen.
- C 1 -C 10 -haloalkyl refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C 1 -C 4 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichlor
- C 1 -C 10 -alkoxy refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached via an oxygen atom.
- Examples include C 1 -C 6 -alkoxy such as methoxy, ethoxy, OCH 2 -C 2 H 5 , OCH(CH 3 ) 2 , n-butoxy, OCH(CH 3 )-C 2 H 5 , OCH 2 -CH(CH 3 ) 2 , OC(CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3
- C 1 -C 10 -haloalkoxy refers to a C 1 -C 10 -alkoxy group as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, C 1 -C 6 -haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
- C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl refers to C 1 -C 6 -alkyl which is substituted by C 1 -C 6 -alkoxy as mentioned above, i.e., for example, CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n-propoxymethyl, CH 2 -OCH(CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH 2 -OC(CH 3 ) 3 , 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxyethyl,
- C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy refers to C 1 -C 6 -alkoxy which is substituted by C 1 -C 6 -alkoxy as mentioned above, i.e., for example, OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH(CH 3 ) 2 , n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH 2 -OC(CH 3 ) 3 , 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy
- C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy refers to C 1 -C 4 -alkoxy which is substituted by C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy as mentioned above, i.e., for example, 2-(2-methoxyethyloxy)ethyloxy, 2-(2-ethoxyethyloxy)ethyloxy;
- C 1 -C 10 -alkylcarbonyl refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) bonded via the carbon atom of the carbonyl group at any bond in the alkyl group.
- C 1 -C 10 -alkoxycarbonyl refers to a straight-chain or branched alkoxy group (as mentioned above) having 1 to 10 carbon atoms attached via the carbon atom of the carbonyl group.
- Examples include (C 1 -C 6 -alkoxy)carbonyl, for example CO-OCH 3 , CO-OC 2 H 5 , COO-CH 2 -C 2 H 5 , CO-OCH(CH 3 ) 2 , n-butoxycarbonyl, CO-OCH(CH 3 )-C 2 H 5 , CO-OCH 2 -CH(CH 3 ) 2 , CO-OC(CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-di
- C 1 -C 10 -alkylthio (C 1 -C 10 -alkylsulfanyl: C 1 -C 10 -alkyl-S-)
- C 1 -C 4 -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio.
- Examples include C 1 -C 6 -alkylsulfinyl: SO-CH 3 , SO-C 2 H 5 , n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methyl
- Examples include C 1 -C 6 -alkylsulfonyl such as SO 2 -CH 3 , SO 2 -C 2 H 5 , n-propylsulfonyl, SO 2 -CH(CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, SO 2 -C(CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-
- C 2 -C 10 -alkenyl refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propeny
- C 2 -C 10 -alkynyl refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-3-yl, 3-methyl
- C 3 -C 10 -cycloalkyl refers to a monocyclic hydrocarbon radical having 3 to 10 carbon atoms, in particular 3 to 8 carbon atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl,
- C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl refers to a C 1 -C 4 -alkyl which carries a C 3 -C 8 -cycloalkyl radical as defined above, for example cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl, 2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)
- phenyl-C 1 -C 4 -alkyl refers to C 1 -C 4 -alkyl which is substituted by phenyl, which may for its part be unsubstituted or carries one, two or three substituents, such as benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)-prop-1-yl, preferably benzyl,
- heterocyclyl refers to a 3- to 7-membered heterocyclic radical which has 3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of these ring members are heteroatoms selected, independently from each other, from the group consisting of oxygen, nitrogen, sulfur and a group NR 5 , wherein R 5 has the meanings as defined above.
- the heterocycle may be a carbon-bonded heterocycle or may be bonded via a heteroatom.
- the heterocycle may be aromatic (heteroaryl) or partially or fully saturated.
- heterocyclyl radical may be fused to a 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring which may carry for their part one, two, three, four, five or six substituents which are selected, independently from another from the group consisting of halogen such as fluorine, chlorine, bromine and C 1 -C 4 -alkyl such as methyl.
- Examples for monocyclic heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl or isoxazolyl.
- non-aromatic rings examples include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothiophenyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyr
- fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring refers to a cyclic radical which carries a fused saturated C 5 -C 7 -carbocycle as defined above, a mono- or diunsaturated C 5 -C 7 -carbocycle or phenyl or to a 5-7-membered heterocyclic ring as defined above.
- C 3 -C 10 -cycloalkyl fused with a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring are indan-1-yl, indan-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl or hydrindanyl and the like.
- phenyl fused with a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring are indan-5-yl, indan-6-yl, dihydronaphthalen-5-yl, dihydronaphthalen-6-yl, 1,2,3,4-tetrahydronaphthalen-5-yl, 1,2,3,4-tetrahydronaphthalen-6-yl, quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyl, benzoxazolyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl, benzimidazolyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochin
- Examples for 3- to 7-membered heterocyclyl carrying a fused-on 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or a 5- to 7-membered heterocyclic ring are quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyl, benzoxazolyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl, benzimidazolyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroisochinolinyl, chromenyl, chromanyl and the like.
- the pesticidal activity of the 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I preference is given to those compounds I, in which the radical R 4 is attached to the nitrogen atom of the amino group via a secondary or tertiary carbon atom.
- R 4 is phenyl, naphthyl, C 3 -C 10 -cycloalkyl, a 3- to 7-membered heterocyclyl or a radical -A-R 4a , wherein A C 2 -C 6 -alkylene which is attached to the nitrogen via a secondary or tertiary carbon atom of the C 2 -C 6 -alkylene chain.
- the C 2 -C 6 -alkylene chain may comprise a heteroatom selected from the group consisting of oxygen and sulfur.
- the compounds comprise the pure R- and S-enantiomers as well as the mixtures of the enantiomers such as the racemic mixtures. Particularly preferred among these are the pure enantiomers.
- a preferred embodiment of the method of the invention uses compounds of the general formula I, wherein R 4 is cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl, wherein the cyclohexyl group and the phenyl group in the last three mentioned radicals may be unsubstituted or may carry one or two substituents which are selected, independently from each other, from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl and phenyloxy, wherein the two last mentioned substituents for their part may be unsubstituted or may carry one or two substituents which are selected independently of each other from the group
- R 4 is a cyclohexyl radical which may carry one or two substituents.
- One substituent is preferably attached to the 4-position of the cyclohexyl radical.
- Particularly preferred substituents of the radical cyclohexyl mentioned for R 4 are, independently of one another, C 1 -C 4 -alkyl, especially methyl, ethyl, isopropyl, sec-butyl and tert-butyl or cyclohexyl-C 1 -C 4 -alkyl.
- the compounds I those are especially preferred, wherein the cyclohexyl radical carries a substituent in the 4-position, said substituent is most preferably attached cis relative to the nitrogen atom.
- 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines in which R 4 is phenyl, benzyl, 1-phenylethyl or 2-phenylethyl which for their part carry one or two of the above defined substituents on the phenyl ring.
- the substituents are preferably selected independently of each other from the group consisting fluorine, chlorine, bromine, C 1 -C 4 -alkyl especially methyl, ethyl, n-propyl, isopropyl, 2-butyl and tert-butyl; C 1 -C 4 -alkoxy, especially methoxy, ethoxy, tert-butoxy, C 1 -C 4 -haloalkyl, especially trifluoromethyl and C 1 -C 4 -haloalkoxy, especially trifluorodifluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy.
- R 4 is 1-phenylethyl which carries at least one substituent as defined above, especially one which has been indicated as preferred. Most preferably said substituent is attached in the 4-position of the phenyl radical. Particularly preferred among these are compounds I in which R 4 is the pure enantiomer or a racemic mixture.
- the radical R4 comprises a phenyl group such as in phenyl, benzyl and 1- or -2-phenylethyl, wherein the the phenyl ring carries at least one substituent which is selected from the group consisting of phenyl, cyclohexyl and phenoxy which for their part may be unsubstituted or may carry in the 2-, 3- or 4-position one or two substituents selected from the group consisting of C 1 -C 4 -alkyl, especially methyl, ethyl, n-propyl or isopropyl, C 1 -C 4 -alkoxy such as methoxy and halogen, especially fluorine, chlorine or bromine.
- a phenyl group such as in phenyl, benzyl and 1- or -2-phenylethyl
- the phenyl ring carries at least one substituent which is selected from the group consisting of phenyl, cyclohexyl and phen
- substituents on the phenyl ring of phenyl, benzyl, 1-phenylethyl, or 2-phenylethyl are: 4-methylphenoxy, 4-ethylphenoxy, 4-isopropylphenoxy, 4-tert-butylphenoxy, 4-fluorophenoxy, 4-chlorophenoxy, 4-bromophenoxy, 2-methylphenoxy, 2-tert-butylphenoxy, 2-ethylphenoxy, 3-ethylphenoxy, 2-bromophenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 3-bromophenoxy, 3,4-difluorophenoxy, 3-chloro-4-fluorophenoxy, 4-bromo-3-chlorophenoxy, 4-chloro-3-fluorophenoxy, 3,4-dichlorophenoxy, 3,4-dimethlyphenoxy, 3-chloro-4-methylphenoxy, 3-methyl-4-chlorophenoxy or 3-methyl-4-bromophenoxy.
- Table A No. R 2 R 4 A-1.
- CH 3 4-C 2 H 5 -C 6 H 4 -CH 2 - A-34. CH 3 4-n-C 3 H 7 -C 6 H 4 -CH 2 - A-35. CH 3 4-isopropyl-C 6 H 4 -CH 2 - A-36. CH 3 4-n-C 4 H 9 -C 6 H 4 -CH 2 - A-37. CH 3 4-isobutyl-C 6 H 4 -CH 2 - A-38. CH 3 4-tert-buyl-C 6 H 4 CH 2 - A-39. CH 3 4-F 3 C-C 6 H 4 CH 2 - A-40. CH 3 4-methoxy-C 6 H 4 CH 2 - A-41.
- CH 3 4-ethoxy-C 6 H 4 CH 2 - A-42. CH 3 4-n-propoxy-C 6 H 4 CH 2 - A-43. CH 3 4-isopropoxy-C 6 H 4 CH 2 - A-44. CH 3 4-n-butoxy-C 6 H 4 CH 2 - A-45. CH 3 4-tert-butoxy-C 6 H 4 CH 2 - A-46. CH 3 4-F-C 6 H 4 CH 2 - A-47. CH 3 4-Cl-C 6 H 4 CH 2 - A-48. CH 3 4-Br-C 6 H 4 CH 2 - A-49. CH 3 3,4-F 2 -C 6 H 3 CH 2 - A-50.
- CH 3 4-(4-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-57. CH 3 4-(4-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-58. CH 3 4-(4-tert-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-59. CH 3 4-(4-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-60. CH 3 4-(4-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-61.
- CH 3 4-(4-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-62. CH 3 4-(4-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-63. CH 3 4-(4-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-64. CH 3 4-(4-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-65. CH 3 4-(4-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-66.
- CH 3 4-(3-CH 3 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-67. CH 3 4-(3-C 2 H 5 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-68. CH 3 4-(3-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-69. CH 3 4-(3-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-70. CH 3 4-(3-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-71.
- CH 3 4-(3-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-72. CH 3 4-(3-tert-butyl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-73. CH 3 4-(3-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-74. CH 3 4-(3-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-75. CH 3 4-(3-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-76.
- CH 3 4-(3-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-77. CH 3 4-(3-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-78. CH 3 4-(3-F-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-79. CH 3 4-(3-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-80. CH 3 4-(3-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-81.
- CH 3 4-(2-CH 3 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-82. CH 3 4-(2-C 2 H 5 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-83. CH 3 4-(2-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-84. CH 3 4-(2-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-85. CH 3 4-(2-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-86.
- CH 3 4-(2-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-87. CH 3 4-(2-tert-butyl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-88. CH 3 4-(2-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-89. CH 3 4-(2-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-90. CH 3 4-(2-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-91.
- CH 3 4-(2-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-92. CH 3 4-(2-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-93. CH 3 4-(2-F-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-94. CH 3 4-(2-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-95. CH 3 4-(2-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-96.
- CH 3 4-(3,4-F 2 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-97. CH 3 4-(3,4-Cl 2 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-98. CH 3 4-(3,4-(CH 3 ) 2 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-99. CH 3 4-(3-F-4-Cl-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-100. CH 3 4-(3-Cl-4-F-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-101.
- CH 3 4-(3-CH 3 -4-Cl-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-102. CH 3 4-(3-Cl-4-CH 3 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-103. CH 3 4-(3-Cl-4-Br-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-104. CH 3 4-(3-CH 3 -4-Br-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-105. CH 3 ( ⁇ ) phenyl-CH(CH 3 )- A-106. CH 3 (R) phenyl-CH(CH 3 )- A-107.
- CH 3 (S) 4-H 5 C 2 -O-phenyl-CH(CH 3 )- A-144. CH 3 ( ⁇ ) 4-n-propoxy-phenyl-CH(CH 3 )- A-145. CH 3 (R) 4-n-propoxy-phenyl-CH(CH 3 )- A-146. CH 3 (S) 4-n-propoxy-phenyl-CH(CH 3 )- A-147. CH 3 ( ⁇ ) 4-n-butoxy-phenyl-CH(CH 3 )- A-148. CH 3 (R) 4-n-butoxyx-phenyl-CH(CH 3 )- A-149. CH 3 (S) 4-n-butoxyphenyl-CH(CH 3 )- A-150.
- CH 3 (R) 4-tert-butoxyx-phenyl-CH(CH 3 )- A-152.
- CH 3 ( ⁇ ) 4-CH 3 -phenyl-CH(CH 3 )- A-154.
- CH 3 (R) 4-C 2 H 5 -phenyl-CH(CH 3 )- A-158.
- CH 3 (S) 4-C 2 H 5 -phenyl-CH(CH 3 )- A-159.
- CH 3 ( ⁇ ) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-160.
- CH 3 (R) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-161.
- CH 3 (S) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-162.
- CH 3 ( ⁇ ) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-163.
- CH 3 (R) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-164.
- CH 3 (S) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-165.
- CH 3 ( ⁇ ) 4-n-C 4 H 9 -phenyl-CH(CH 3 )- A-166.
- CH 3 (R) 4-n-C 4 H 9 -phenyl-CH(CH 3 )- A-167.
- CH 3 (S) 4-n-C 4 H 9 -phenyl-CH(CH 3 )- A-168.
- CH 3 ( ⁇ ) 4-tert-C 4 H 9 -phenyl-CH(CH 3 )- A-169.
- CH 3 (S) 4-Difluoromethoxyphenyl-CH(CH 3 )- A-204.
- CH 3 ( ⁇ ) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-205.
- CH 3 (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-206.
- CH 3 (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-207.
- CH 3 ( ⁇ ) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-208.
- CH 3 (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-209.
- CH 3 (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-210.
- CH 3 ( ⁇ ) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-211.
- CH 3 (R) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-212.
- CH 3 (S) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-213.
- CH 3 ( ⁇ ) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-214.
- CH 3 (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-215.
- CH 3 (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-216.
- CH 3 (R) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-218.
- CH 3 (S) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-219.
- CH 3 (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-221.
- CH 3 (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-222.
- CH 3 ( ⁇ ) (2-methyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-223.
- CH 3 (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-224.
- CH 3 (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-225.
- CH 3 (R) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-227.
- CH 3 (S) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-228.
- CH 3 (R) (2,2-difluorobenzodioxole-5-yl)CH(C 2 H 5 )- A-230.
- CH 3 4-n-C 4 H 9 O-C 6 H 4 CH 2 CH 2 - A-239.
- CH 3 CH 2 4-n-butylcyclohexyl- A-262. CH 3 CH 2 cis-4-n-butylcyclohexyl- A-263. CH 3 CH 2 trans-4-n-butylcyclohexyl- A-264. CH 3 CH 2 4-(2-butyl)cyclohexyl- A-265. CH 3 CH 2 cis-4-(2-butyl)cyclohexyl- A-266. CH 3 CH 2 trans-4-(2-butyl)cyclohexyl- A-267. CH 3 CH 2 4-tert-butylcyclohexyl- A-268. CH 3 CH 2 cis-4-tert-butylcyclohexyl- A-269.
- CH 3 CH 2 4-(4-CH 3 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-301.
- CH 3 CH 2 4-(4-C 2 H 5 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-302.
- CH 3 CH 2 4-(4-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-303.
- CH 3 CH 2 4-(4-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-304.
- CH 3 CH 2 4-(4-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-305.
- CH 3 CH 2 4-(4-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-310.
- CH 3 CH 2 4-(4-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-311.
- CH 3 CH 2 4-(4-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-312.
- CH 3 CH 2 4-(4-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-314.
- CH 3 CH 2 4-(3-CH 3 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-315.
- CH 3 CH 2 4-(3-C 2 H 5 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-316.
- CH 3 CH 2 4-(3-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-317.
- CH 3 CH 2 4-(3-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-318.
- CH 3 CH 2 4-(3-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-319.
- CH 3 CH 2 4-(3-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-320.
- CH 3 CH 2 4-(3-tert-butyl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-321.
- CH 3 CH 2 4-(3-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-322.
- CH 3 CH 2 4-(3-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-323.
- CH 3 CH 2 4-(3-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-324.
- CH 3 CH 2 4-(3-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-325.
- CH 3 CH 2 4-(3-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-326.
- CH 3 CH 2 4-(3-F-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-327.
- CH 3 CH 2 4-(3-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-328.
- CH 3 CH 2 4-(3-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-329.
- CH 3 CH 2 4-(2-CH 3 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-330.
- CH 3 CH 2 4-(2-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-332.
- CH 3 CH 2 4-(2-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-333.
- CH 3 CH 2 4-(2-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-334.
- CH 3 CH 2 4-(2-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-335.
- CH 3 CH 2 4-(2-tert-butyl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-336.
- CH 3 CH 2 4-(2-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-337.
- CH 3 CH 2 4-(2-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-338.
- CH 3 CH 2 4-(2-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-339.
- CH 3 CH 2 4-(2-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-340.
- CH 3 CH 2 4-(2-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-341.
- CH 3 CH 2 4-(2-F-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-342.
- CH 3 CH 2 4-(2-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-343.
- CH 3 CH 2 4-(2-Br-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-344.
- CH 3 CH 2 4-(3,4-Cl 2 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-346.
- CH 3 CH 2 4-(3,4-(CH 3 ) 2 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-347.
- CH 3 CH 2 4-(3-F-4-Cl-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-348.
- CH 3 CH 2 4-(3-Cl-4-F-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-349.
- CH 3 CH 2 4-(3-CH 3 -4-Cl-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-350.
- CH 3 CH 2 4-(3-Cl-4-CH 3 -C 6 H 3 -O)-C 6 H 4 -CH 2 - A-351.
- CH 3 CH 2 4-(3-Cl-4-Br-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-352.
- CH 3 CH 2 4-(3-CH 3 -4-Br-C 6 H 3 -O)-C 6 H 4 -CH 2 - A-353.
- CH 3 CH 2 (S) phenyl-CH(CH 3 )- A-356.
- CH 3 CH 2 (R) 4-n-butoxyx-phenyl-CH(CH 3 )- A-397.
- CH 3 CH 2 ( ⁇ ) 4-tert-butoxy-phenyl-CH(CH 3 )- A-399.
- CH 3 CH 2 (S) 4-tert-butoxyphenyl-CH(CH 3 )- A-401.
- CH 3 CH 2 (R) 4-CF 3 -phenyl-CH(CH 3 )- A-427.
- CH 3 CH 2 (S) 4-Difluoromethoxyphenyl-CH(CH 3 )- A-452.
- CH 3 CH 2 ( ⁇ ) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-453.
- CH 3 CH 2 (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-454.
- CH 3 CH 2 (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-455.
- CH 3 CH 2 ( ⁇ ) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-456.
- CH 3 CH 2 (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-457.
- CH 3 CH 2 (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-458.
- CH 3 CH 2 ( ⁇ ) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-459.
- CH 3 CH 2 (R) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-460.
- CH 3 CH 2 (S) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-461.
- CH 3 CH 2 ( ⁇ ) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH 3 )- A-462.
- CH 3 CH 2 (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH 3 )- A-463.
- CH 3 CH 2 (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH 3 )- A-464.
- CH 3 CH 2 (R) (1,1,4,4,7-pentamethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-466.
- CH 3 CH 2 (S) (1,1,4,4,7-pentamethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-467.
- CH 3 CH 2 (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin- 6-yl)-CH(CH 3 )- A-469.
- CH 3 CH 2 (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin- 6-yl)-CH(CH 3 )- A-470.
- CH 3 CHF 4-(4-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-551.
- CH 3 CHF 4-(4-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-552.
- CH 3 CHF 4-(4-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-553.
- CH 3 CHF 4-(4-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-554.
- CH 3 CHF 4-(4-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-559.
- CH 3 CHF 4-(4-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-560.
- CH 3 CHF 4-(4-Cl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-561.
- CH 3 CHF 4-(3-C 2 H 5 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-564.
- CH 3 CHF 4-(3-n-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-565.
- CH 3 CHF 4-(3-iso-C 3 H 7 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-566.
- CH 3 CHF 4-(3-n-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-567.
- CH 3 CHF 4-(3-iso-C 4 H 9 -C 6 H 4 -O)-C 6 H 4 -CH 2 - A-568.
- CH 3 CHF 4-(3-tert-butyl-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-569.
- CH 3 CHF 4-(3-H 3 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-570.
- CH 3 CHF 4-(3-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-571.
- CH 3 CHF 4-(3-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-572.
- CH 3 CHF 4-(3-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-573.
- CH 3 CHF 4-(3-tert-butoxy-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-574.
- CH 3 CHF 4-(2-H 3 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-586.
- CH 3 CHF 4-(2-H 3 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-587.
- CH 3 CHF 4-(2-H 3 C-H 2 C-H 2 C-H 2 C-O-C 6 H 4 -O)-C 6 H 4 -CH 2 - A-588.
- CH 3 CHF (R) 4-H 5 C 2 -O-phenyl-CH(CH 3 )- A-639.
- CH 3 CHF (S) 4-H 5 C 2 -O-phenyl-CH(CH 3 )- A-640.
- CH 3 CHF ( ⁇ ) 4-n-propoxy-phenyl-CH(CH 3 )- A-641.
- CH 3 CHF (R) 4-n-propoxy-phenyl-CH(CH 3 )- A-642.
- CH 3 CHF (S) 4-n-propoxy-phenyl-CH(CH 3 )- A-643.
- CH 3 CHF ( ⁇ ) 4-n-butoxy-phenyl-CH(CH 3 )- A-644.
- CH 3 CHF (R) 4-n-butoxyx-phenyl-CH(CH 3 )- A-645.
- CH 3 CHF (S) 4-n-butoxyphenyl-CH(CH 3 )- A-646.
- CH 3 CHF ( ⁇ ) 4-tert-butoxy-phenyl-CH(CH 3 )- A-647.
- CH 3 CHF (R) 4-tert-butoxyx-phenyl-CH(CH 3 )- A-648.
- CH 3 CHF (S) 4-tert-butoxyphenyl-CH(CH 3 )- A-649.
- CH 3 CHF ( ⁇ ) 4-CH 3 -phenyl-CH(CH 3 )- A-650.
- CH 3 CHF (R) 4-CH 3 -phenyl-CH(CH 3 )- A-651.
- CH 3 CHF (S) 4-CH 3 -phenyl-CH(CH 3 )- A-652.
- CH 3 CHF ( ⁇ ) 4-C 2 H 5 -phenyl-CH(CH 3 )- A-653.
- CH 3 CHF (R) 4-C 2 H 5 -phenyl-CH(CH 3 )- A-654.
- CH 3 CHF (S) 4-C 2 H 5 -phenyl-CH(CH 3 )- A-655.
- CH 3 CHF ( ⁇ ) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-656.
- CH 3 CHF (R) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-657.
- CH 3 CHF (S) 4-n-C 3 H 7 -phenyl-CH(CH 3 )- A-658.
- CH 3 CHF ( ⁇ ) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-659.
- CH 3 CHF (R) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-660.
- CH 3 CHF (S) 4-iso-C 3 H 7 -phenyl-CH(CH 3 )- A-661.
- CH 3 CHF ( ⁇ ) 4-n-C 4 H 9 -phenyl-CH(CH 3 )- A-662.
- CH 3 CHF (R) 4-cycl.-C 6 H 11 -phenyl-CH(CH 3 )- A-669.
- CH 3 CHF (S) 4-cycl.-C 6 H 11 -phenyl-CH(CH 3 )- A-670.
- CH 3 CHF ( ⁇ ) 4-OCF 3 -phenyl-CH(CH 3 )- A-671.
- CH 3 CHF (R) 4-OCF 3 -phenyl-CH(CH 3 )- A-672.
- CH 3 CHF (S) 4-OCF 3 -phenyl-CH(CH 3 )- A-673.
- CH 3 CHF ( ⁇ ) 4-CF 3 -phenyl-CH(CH 3 )- A-674.
- CH 3 CHF ( ⁇ ) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-701.
- CH 3 CHF (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-702.
- CH 3 CHF (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH 3 )- A-703.
- CH 3 CHF ( ⁇ ) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-704.
- CH 3 CHF (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-705.
- CH 3 CHF (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH 3 )- A-706.
- CH 3 CHF ( ⁇ ) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-707.
- CH 3 CHF (R) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-708.
- CH 3 CHF (S) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-709.
- CH 3 CHF (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-711.
- CH 3 CHF (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-712.
- CH 3 CHF (R) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-714.
- CH 3 CHF (S) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-715.
- CH 3 CHF ( ⁇ ) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-716.
- CH 3 CHF (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-717.
- CH 3 CHF (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH 3 )- A-718.
- CH 3 CHF (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-720.
- CH 3 CHF (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-721.
- CH 3 CHF (R) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-723.
- CH 3 CHF (S) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH 3 )- A-724.
- CH 3 CHF ( ⁇ ) (2,2-difluorobenzodioxole-5-yl)CH(C 2 H 5 )- A-725.
- CH 3 CHF (R) (2,2-difluorobenzodioxole-6-yl)CH(C 2 H 5 )- A-726.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula Ib, where X is Cl, R 1 is CH 3 and R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula Ic, where X is Cl, R 1 is OCH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula , where X is Cl, R 1 is SCH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is SOCH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is SO 2 CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is CF 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is CN, R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OH, R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCHF 2 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCF 2 CHF 2 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCF 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCH 2 C 6 H 5 , R 3 is H, R 2 and R 4 together have the mean-ings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCH 2 CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCH 2 C ⁇ CH, R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is OCH(CH 3 ) 2 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is O-CH 2 CH 2 -O-CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is O-CH 2 CH 2 -O-CH 2 CH 2 -O-CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is S-CH 2 CH 2 -O-CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is S-CH 2 C(O)-O-CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is S-CH 2 CH 2 C(O)-O-CH 3 , R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R 1 is S-CH 2 C(O)-OH, R 3 is H, R 2 and R 4 together have the meanings given in one row of Table A.
- 6-halogeno-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I as used in the method according to the present invention can be prepared, for example, similarly to a process described in Pharmazie, 1971, 26, 534 ff or in DD 99 794 .
- the synthesis is shown in Scheme 1.
- Suitable solvents are all solvents which are inert under the reaction conditions, such as aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, petrol ether, cyclohexane, benzene, toluene, xylenes, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, cyclic ethers, such as tetrahydrofuran or dioxane, halogenated hydrocarbons such as dichloromethane or trichloromethane or C 1 -C 4 -alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol or tert-butanol, water or mixtures of these solvents.
- aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, petrol ether, cyclohexan
- reaction is carried out in the presence of a solvent. If the reaction is carried out in the absence of a solvent, the amine (III) is employed in a large excess, based on 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidin II.
- Suitable bases include organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, 2,3-lutidine, 2,4-lutidine or 2,5-lutidine and inorganic bases, for example alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and sodium carbonate, calcium carbonate and alkali metal hydrogencarbonates such as sodium hydrogen carbonate.
- An excess of the amine III may serve as base.
- the reaction temperature is usually in the range of from 0°C to the boiling of the solvent, preferably of from 20 to the 120°C.
- the molar ratio of amine III to 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II is generally at least 0.9:1, preferably at least 1:1. It may be advantageous to employ the amine III in a slight excess, for example of up to 20%, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II.
- the base is employed in at least equimolar amount to a 2-fold molar excess, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II. It may be advantageous to employ the base in a slight excess, for example up to 30%, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II.
- reaction mixtures are worked up in a customary manner, for example by adding diluted acids, for example mineral acids such as diluted hydrochloric acid, hydrobromic acid and sulfuric acid or aqueous organic acids such as trifluoroacetic acid or acetic acid, aqueous hydrochloric acid being preferred, phase separation and, if appropriate, chromatographic purification, recrystallization, trituration or digestion.
- diluted acids for example mineral acids such as diluted hydrochloric acid, hydrobromic acid and sulfuric acid or aqueous organic acids such as trifluoroacetic acid or acetic acid, aqueous hydrochloric acid being preferred, phase separation and, if appropriate, chromatographic purification, recrystallization, trituration or digestion.
- diluted acids for example mineral acids such as diluted hydrochloric acid, hydrobromic acid and sulfuric acid or aqueous organic acids such as trifluoroacetic acid or acetic acid, aqueous hydrochloric acid being preferred, phase separation and,
- the compounds of formula I may be obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.
- amines of the formula III which are employed as starting materials are commercially available.
- Other may be prepared by processes known in the art, for example, by conversion of the corresponding alcohols into its tosylates which are then converted to the phthalimido derivatives.
- the phthalimido derivatives are converted to the desired amines by using hydrazine or any other suitable cleavage agent using conventional methods [e.g. J. Am. Soc., Vol. 117, p. 7025 (1995 ); WO 93/20804 ]; by reduction of the corresponding nitriles [see, Heterocycles, Vol. 35, p. 2 (1993 ); Synthetic Commun., Vol. 25, p.
- the radical R 4 may be introduced by Grignard reaction to nitriles or carboxylic acid anhydrides (see J. Org. Chem. p. 5056 (1992 ); Tetrahedron Lett., S. 29933 (1995 )). If individual amines III are not disclosed in the cited literature they can be either obtained by routes described above or they can be prepared by derivatization of other compounds III or by customary modifications of the synthesis routes described above.
- the starting materials of the formula II may be prepared in two steps, in analogy to the process described in Chem. Pharm. Bull. 1959, Vol. 7, p. 903 .
- the synthesis is shown in Scheme 2.
- the variables R 1 , R 2 and X are as defined above, X' is halogen, R is alkyl, preferably C 1 -C 6 -alkyl, in particular methyl or ethyl and Hal means a halogenating agent.
- the 5-aminotriazole of the general formula IV is reacted with the malonic ester of the general formula V.
- the reaction may be carried out under alkaline conditions, preferably using high boiling tertiary amines as for example tri-n-butylamine.
- the 5-aminotriazoles IV are commercially available or can be prepared in analogy to the methods which are well known in the art.
- halogenating agent preferably with a brominating or chlorinating agent.
- Suitable halogenating agents include inorganic acid halides, preferably acid chlorides or acide bromides such as thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosphorus pentachloride or phosphorus tribromide, phosphorus trichloride and mixtures of these.
- phosphorus oxychloride is used as a halogenating agent
- the reaction is preferably carried out in the presence of a mineral acid, such as polyphosphoric acid and pyridinium salts such as pyridinium bromide or chloride.
- Preferred halogenating agents are POCl 3 , PCl 3 /Cl 2 or PCl 5 and mixtures of these.
- the reaction can be carried out in the presence or absence of a solvent.
- the acid halides thionylchloride, phoshorus trichloride or phosphoryl chloride may simultaneous act as solvent. Suitable solvents are furthermore acetonitrile or dichloromethane.
- the halogenating agent is generally used in at least equimolar amounts, based on the 6-halogeno-7-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine of the general formula VI.
- the reaction is suitable carried out at a temperature in the range from 0°C to 150°C, the preferred reaction temperature being from 80°C to 125°C.
- the compounds of the general formula I may be used for controlling animal pests.
- Animal pests include harmful insects, acaridae and arachnids
- the invention further provides agriculturally composition for combating animal pests, especially insects, arachnids and/or acaridae which comprises such amount of at least one compound of the general formula I' as defined in claim 17 or at least an agriculturally useful salt of I' as defined in claim 17 and a least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant.
- compositions may contain a single active compound of the general formula I or a mixture of several active compounds I according to the present invention.
- the composition according to the present invention may comprise an individual isomer or mixtures of isomers.
- the 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines and the pestidicidal compositions comprising them are effective agents for controlling animal pests.
- Animal pests controlled by the compounds of formula I include for example:
- the compounds of the formula I are preferably used for controlling pests of the orders Lepidoptera, Coleoptera, Homoptera and Acarina.
- the compounds of formula (I) or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula (I).
- crop refers both to growing and harvested crops.
- the animal pest especially the insect, acaridae, arachnid, plant and/or soil or water in which the plant is growing can be contacted with the present compound(s) I or composition(s) containing them by any application method known in the art.
- "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest, especially the insect, acaridae and/or arachnid, and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest, especially the insect, acaridae, and/or arachnid, and/or plant).
- animal pests especially insects, acaridae or arachnids may be controlled by contacting the target pest, its food supply or its locus with a pesticidally effective amount of compounds of formula (I).
- the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
- “Locus” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
- Effective amounts suitable for use in the method of invention may vary depending upon the particular formula I compound, target pest, method of application, application timing, weather conditions, animal pest habitat, especially insect, arachnid or acarid habitat, or the like.
- the rate of application of the compounds I and/or compositions according to this invention may be in the range of about 0.1 g to about 4000 g per hectare, desirably from about 25 g to about 600 g per hectare, more desirably from about 50 g to about 500 g per hectare.
- the typical rate of application is of from about 1 g to about 500 g per kilogram of seeds, desirably from about 2 g to about 300 g per kilogram of seeds, more desirably from about 10 g to about 200 g per kilogram of seeds.
- Customary application rates in the protection of materials are, for example, from about 0.001 g to about 2000 g, desirably from about 0.005 g to about 1000 g, of active compound per cubic meter of treated material.
- the compounds I or the pesticidal compositions comprising them can be used, for example in the form of solutions, emulsions, microemulsions, suspensions, flowable concentrates, dusts, powders, pastes and granules.
- the use form depends on the particular purpose; in any case, it should guarantee a fine and uniform distribution of the compound according to the invention.
- the pesticidal composition for combating animal pests, especially insects, acaridae and/or arachnids contains such an amount of at least one compound of the general formula I or an agriculturally useful salt of I and auxiliaries which are usually used in formulating pesticidal composition.
- the formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent.
- auxiliary solvents e.g. water
- solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e.g.
- kaolins kaolins, clays, talc, chalk
- ground synthetic minerals e.g. highly-disperse silica, silicates
- emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
- Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol
- Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
- benzene toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
- strongly polar solvents e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
- Powders, materials for scattering and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
- Granules e.g. coated granules, compacted granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
- solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
- mineral earths such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,
- compositions of the present invention include a formula I compound of this invention (or combinations thereof) admixed with one or more agronomically acceptable inert, solid or liquid carriers.
- Those compositions contain a pesticidally effective amount of said compound or compounds, which amount may vary depending upon the particular compound, target pest, and method of use.
- the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient.
- the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- a compound according to the invention 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).
- VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl- ⁇ -pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient).
- 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene- ⁇ -sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.
- the active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, scattering or pouring.
- the use forms depend entirely on the intended purposes; in any case, this is intended to guarantee the finest possible distribution of the active ingredients according to the invention.
- Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
- emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
- concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil and such concentrates are suitable for dilution with water.
- the active ingredient concentrations in the ready-to-use products can be varied within substantial ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.
- the active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even the active ingredient without additives.
- UUV ultra-low-volume process
- compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
- additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix).
- the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
- agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
- Example 105 (6-chloro-5-ethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-[(2-(4-trifluoromethoxyphenyl)-ethyl]-amine
- H CH 3 4-((CH 3 ) 2 CH)-cyclohexyl- 109-112 7.
- H CH 3 trans-4-tert-butylcyclohexyl- 138-140 11.
- H C 2 H 5 4-methylcyclohexyl- 150-152 19.
- H C 2 H 5 4-(cyclohexyl-C(CH 3 ) 2 )-cyclohexyl- 205-209 20.
- H C 2 H 5 4-((CH 3 ) 2 CH)-cyclohexyl- 140-144 21.
- H CF 3 4-tert-butylcyclohexyl- 155-157 25.
- H CF 3 4-methylcyclohexyl- 171-173 26.
- H CF 3 4-(cyclohexyl-C(CH 3 ) 2 )-cyclohexyl- 191-193 27.
- H CF 3 4-((CH 3 ) 2 CH)-cyclohexyl- 160-161 28.
- H CH 3 4-tert-butylbenzyl 164-168 58. H CH 3 4-tert-butoxybenzyl 102-105 59. H CH 3 3,4-Cl 2 C 6 H 3 -CH 2 - 195-200 60. H CH 3 4-chlorobenzyl 171-175 61. H CH 3 4-(4-methoxyphenoxy)phenyl-CH 2 - 132-136 62. H CH 3 4-(4-tert-butylphenoxy)phenyl-CH 2 - resinous 63. H CH 3 4-(4-bromophenoxy)phenyl-CH 2 - 150-152 64. H CH 3 4-(4-ethylphenoxy)phenyl-CH 2 - 160-162 65.
- H CH 3 4-(4-methylphenoxy)phenyl-CH 2 156-158 66. H CH 3 4-(4-chlorophenoxy)phenyl-CH 2 - 146-148 67. H CH 3 4-(2-ethylphenoxy)phenyl-CH 2 - 157-159 68. H CH 3 4-(3-ethylphenoxy)phenyl-CH 2 - resinous 69. H CH 3 4-(2-bromophenoxy)phenyl-CH 2 - 162-164 70. H CH 3 4-(3-chlorophenoxy)phenyl-CH 2 - 167-168 71. H CH 3 4-(2-methylphenoxy)phenyl-CH 2 - 155-161 72.
- H CH 3 4-(2-tert-butylphenoxy)phenyl-CH 2 - 152-155 73.
- H CH 3 4-(2-chlorophenoxy)phenyl-CH 2 - 165-167 74.
- H CH 3 4-(3-fluorophenoxy)phenyl-CH 2 - 167-174 75.
- H CH 3 4-(3-bromophenoxy)phenyl-CH 2 158-160 76.
- H CH 3 4-(4-isopropylphenoxy)phenyl-CH 2 - 160-163 77.
- H CH 3 4-(3-fluoro-4-chlorophenoxy)phenyl-CH 2 - 106-108 78.
- H CH 3 4-(3-chloro-4-bromophenoxy)phenyl-CH 2 - 135-138 79.
- H CH 3 4-(3-chloro-4-methylphenoxy)phenyl-CH 2 - 138-140 80.
- H CH 3 4-(3,4-difluorophenoxy)phenyl-CH 2 - 121-124 81.
- H CH 3 4-(3-methyl-4-chlorophenoxy)phenyl-CH 2 - 145-148 82.
- H CH 3 4-(3,4-dimethylphenoxy)phenyl-CH 2 - 157-159 83.
- H CH 3 4-(3-chloro-4-fluorophenoxy)phenyl-CH 2 - 122-125 84.
- H CH 3 4-(3,4-dichlorophenoxy)phenyl-CH 2 - resinous 85.
- H CH 3 4-(3-methyl-4-bromophenoxy)phenyl-CH 2 - 158-160 86.
- H C 2 H 5 4-(4-ethylphenoxy)phenyl-CH 2 - resinous 87.
- H C 2 H 5 4-tert-butylphenyl-CH 2 - 111-113 91.
- H C 2 H 5 4-(4-tert-butoxy)-C 6 H 4 -CH 2 - 80-85 92.
- H C 2 H 5 4-Cl-C 6 H 4 -CH 2 - 142-146 93.
- H C 2 H 5 4-(4-methoxyphenoxy)phenyl-CH 2 - 100-106 94.
- H CF 3 4-tert-butylphenyl-CH 2 - 109-111 96.
- H CH 3 C 6 H 5 -CH 2 CH 2 - 161-163 97.
- H CH 3 4-Cl-C 6 H 4 -CH 2 CH 2 - 165-167 98.
- H CH 3 4-F-C 6 H 4 -CH 2 CH 2 - 180-182 99.
- H C 2 H 5 4-F-C 6 H 4 -CH 2 CH 2 - 162-165 104.
- H C 2 H 5 4-trifluoromethoxy-C 6 H 4 CH 2 CH 2 - 186-187 106.
- H C 2 H 5 4-tert-butylphenyl-CH 2 CH 2 - 172-174 110.
- H CF 3 4-tert-butylphenyl-CH 2 CH 2 - 176-178 111.
- H C 2 H 5 4-F 3 C-O-C 6 H 4 -CH(CH 3 )- 122-124 171.
- H C 2 H 5 4-tert-butyl-C 6 H 4 -CH(CH 3 )- 93-96 172.
- H CH 3 4-(H 3 C) 2 CH-C 6 H 4 -CH(CH 3 )- Oil 203.
- H C 2 H 5 4-(H 3 C) 2 CH-C 6 H 4 -CH(CH 3 )- 75-77 204.
- H CH 3 110-112 205.
- H C 2 H 5 Oil 206.
- H CH 3 (S)-2,4-Cl 2 -C 6 H 3 -CH(CH 3 )- 92-94 211.
- H C 2 H 5 (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH 3 )- Oil 245.
- H C 2 H 5 4-Cl-2-F-C 6 H 3 -CH(CH 3 )- 97-99 249.
- H CH 3 4-F 2 HC-CF 2 O-C 6 H 4 -CH(CH 3 )- 85-86 268.
- H C 2 H 5 4-F 2 HC-CF 2 O-C 6 H 4 -CH(CH 3 )- 82-83 m.p.
- Cotton plants in the cotyledon stage (variety 'Delta Pine') are infested with approximately 100 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The cotyledons of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.
- Lima bean plants in the 1 st leaf-pair stage (variety 'Henderson') are infested with approximately 100 laboratory-reared mites per leaf by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The foliage of the intact plants is dipped into gradient solutions of the test compound. Mite mortality is determined after 5 days.
- Pepper plants in the 2 nd leaf-pair stage (variety 'California Wonder') are infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The leaves of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.
- Nasturtium plants in the 1 st leaf-pair stage are infested with approximately 25 laboratory-reared aphids by placing infested cut plants on top of the test plants. The cut plants are removed after 24 hr. The foliage and stem of the test plants are dipped into gradient solutions of the test compound. Aphid mortality is determined after 3 days.
- Foliage of two Sieva lima beans plants at the first expanded true-leaf stage that are contained within a single 3.8 cm square plastic pot are dipped into the test solution with agitation for 3 seconds and allowed to dry in a hood. The pot is then placed in a 25.4 cm plastic zipper top bag and infested with ten 2 nd instar caterpillars. At 5 days, observations are made of mortality, reduced feeding, or any interference with normal molting.
- Potted rice plants of 3-4 weeks of age are sprayed with 10 ml of the test solution using air driven hand atomizer (Devillbis atomizer) at 1.7 bar.
- the treated plants are allowed to dry for about 1 hour and covered with Mylar cages.
- the plants are inoculated with 10 adults of each species (5 male and 5 females) and kept at 25-27oC and 50-60% humidity for 3 days. Mortality is assed after 24, 48 and 72 hours after treatment. Dead insects are usually found in the water surface. Each treatment is replicated once.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Catching Or Destruction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
- The present invention relates to 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests.
- Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects, acaridae and/or arachnids are difficult to be effectively controlled.
- It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects, arachnids and acaridae.
-
DD 55 956 DD 99 794 FR 1567021 -
WO 03/039259 -
WO 02/50077 US 4,144,330 discloses insecticidal and acaricidal 5,7-dimethyl- [1,2,4]-triazolo[1,5a]-pyrimidine phosphoric acid derivatives. - So far no 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines have been described, which are useful for combating animal pests, especially for combating insects, arachnids and/or acaridae.
-
- X
- is halogen;
- R1
- is hydrogen, halogen, OH, CN, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C2-C10-alkenyl, phenyl, phenoxy, benzyloxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy or C2-C10-alkynyl, wherein C1-C10-alkylthio, C1-C10-alkylsulfinyl and C1-C10-alkylsulfonyl may be unsubstituted or partially or completely substituted with halogen and/or may carry a group selected from C1-C4-alkoxy, C1-C4-alkoxycarbonyl or COOH, in particular hydrogen, halogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C2-C10-alkenyl or C2-C10-alkynyl;
- R2
- is C1-C10-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C10-cycloalkyl, C2-C10-alkenyl or C2-C10-alkynyl;
- R3
- is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl or arylcarbonyl;
- R4
- is C3-C10-cycloalkyl, phenyl, naphthyl, 3- to 7-membered heterocyclyl or a radical of the formula -A-R4a, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3- to 7-membered heterocyclyl to be unsubstituted or to carry 1, 2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkyl, C1-C10-haloalkoxy, amino, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen,
and wherein heterocyclyl contains 1, 2 or 3 heteroatoms selected, independently from each other, from the group consisting of oxygen, sulfur, nitrogen and a group NR5,
it being also possible for C3-C10-cycloalkyl, phenyl and 3- to 7-membered heterocyclyl to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl; wherein
A is a C1-C6-alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfur;
R4a is C3-C10-cycloalkyl, phenyl, naphthyl or 3- to 7-membered heterocyclyl, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3- to 7-membered heterocyclyl to be unsubstituted or to carry 1, 2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkyl, C1-C10-haloalkoxy, amino, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen,
and wherein heterocyclyl contains 1, 2 or 3 heteroatoms selected, independently from each other, from the group consisting of oxygen, sulfur, nitrogen and a group NR5,
it being also possible for C3-C10-cycloalkyl, phenyl and 3- to 7-membered heterocyclyl to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl; and
R5 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; - Therefore, the present invention relates to the use of the compounds of formula I and of the salts thereof for combating animal pests and also to a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I and/or at least one agriculturally acceptable salt thereof.
- The 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I as defined herein and the agriculturally acceptable salts thereof are particularly useful for combating animal pests which are harmful to crops. Therefore the present invention also relates to the use of the compounds of the general formula I for protecting crops from attack or infestation by animal pests. Thus, the present invention provides a method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of a 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I and/or at least one salt thereof.
-
- Furthermore, the invention relates to agricultural compositions, preferably in the form of directly sprayable solutions, emulsions, pastes oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprise at least one 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidine of the general formula (I)' as defined above, admixed with one or more agronomically acceptable inert, solid or liquid carrier(s) and, if desired, at least one surfactant.
- In the substituents, the compounds of the general formula I may have for a given constitution different spatial arrangement of the atoms, e.g. they may carry one or more centers of chirality, in which case they are present as mixtures of stereoisomers, such as enantiomers or diastereomers. The present invention provides both the pure stereoisomers, e.g. the pure enantiomes or diastereomers, and mixtures thereof.
- Salts of the compounds of the formula I which are suitable for the use according to the invention are especially agriculturally acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question.
- Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention, which are useful for combating harmful insects or arachnids. Thus, suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which may, if desired, carry one to four C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae la and Ib with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
- The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.
- The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
- Examples of other meanings are :
- The term "C1-C10-alkyl" as used herein and the alkyl moieties of alkylamino and dialkylamino refer to a saturated straight-chain or branched hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, especially 1 to 4 carbon groups, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C1-C4-alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.
- The term "C1-C6-alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfur" as used herein refers, for example, to methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,1-diyl, 1-methylpropane-1,2-diyl, 1-methylpropane-2,2-diyl, 1-methylpropane-1,1-diyl, pentane-1,1-diyl, pentane-1,2-diyl, pentane-1,3-diyl, pentane-1,5-diyl, pentane-2,3-diyl, pentane-2,2-diyl, 1-methylbutane-1,1-diyl, 1-methylbutane-1,2-diyl, 1-methylbutane-1,3-diyl, 1-methylbutane-1,4-diyl, 2-methylbutane-1,1-diyl, 2-methylbutane-1,2-diyl, 2-methylbutane-1,3-diyl, 2-methylbutane-1,4-diyl, 2,2-dimethylpropane-1,1-diyl, 2,2-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,3-diyl, 1,1-dimethylpropane-1,2-diyl, 2,3-dimethylpropane-1,3-diyl, 2,3-dimethylpropane-1,2-diyl, 1,3-dimethylpropane-1,3-diyl, hexane-1,1-diyl, hexane-1,2-diyl, hexane-1,3-diyl, hexane-1,4-diyl, hexane-1,5-diyl, hexane-1,6-diyl, hexane-2,5-diyl, 2-methylpentane-1,1-diyl, 1-methylpentane-1,2-diyl, 1-methylpentane-1,3-diyl, 1-methylpentane-1,4-diyl, 1-methylpentane-1,5-diyl, 2-methylpentane-1,1-diyl, 2-methylpentane-1,2-diyl, 2-methylpentane-1,3-diyl, 2-methylpentane-1,4-diyl, 2-methylpentane-1,5-diyl, 3-methylpentane-1,1-diyl, 3-methylpentane-1,2-diyl, 3-methylpentane-1,3-diyl, 3-methylpentane-1,4-diyl, 3-methylpentane-1,5-diyl, 1,1-dimethylbutane-1,2-diyl, 1,1-dimethylbutane-1,3-diyl, 1,1-dimethylbutane-1,4-diyl, 1,2-dimethylbutane-1,1-diyl, 1,2-dimethylbutane-1,2-diyl, 1,2-dimethylbutane-1,3-diyl, 1,2-dimethylbutane-1,4-diyl, 1,3-dimethylbutane-1,1-diyl, 1,3-dimethylbutane-1,2-diyl, 1,3-dimethylbutane-1,3-diyl, 1,3-dimethylbutane-1,4-diyl, 1-ethylbutane-1,1-diyl, 1-ethylbutane-1,2-diyl, 1-ethylbutane-1,3-diyl, 1-ethylbutane-1,4-diyl, 2-ethylbutane-1,1-diyl, 2-ethylbutane-1,2-diyl, 2-ethylbutane-1,3-diyl, 2-ethylbutane-1,4-diyl, 2-ethylbutane-2,3-diyl, 2,2-dimethylbutane-1,1-diyl, 2,2-dimethylbutane-1,3-diyl, 2,2-dimethylbutane-1,4-diyl, 1-isopropylpropane-1,1-diyl, 1-isopropylpropane-1,2-diyl, 1-isopropylpropane-1,3-diyl, 2-isopropylpropane-1,1-diyl, 2-isopropylpropane-1,2-diyl, 2-isopropylpropane-1,3-diyl, 1,2,3-trimethylpropane-1,1-diyl, 1,2,3-trimethylpropane-1,2-diyl or 1,2,3-trimethylpropane-1,3-diyl, preferably ethane-1,1-diyl or propane-1,1-diyl.
- When the C1-C6-alkylene group comprises a heteroatom, the heteroatom can be arranged in the alkylene chain at any position or at the end of the chain so that it connects the alkylene chain to the radical R4a. Preferably, the heteroatom is not arranged at the end of the alkylene chain. The heteroatom is preferably oxygen.
- The term "C1-C10-haloalkyl" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C1-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like.
- The term "C1-C2-fluoroalkyl" as used herein refers to a C1-C2-alkyl which carries 1, 2, 3, 4 or 5 fluorine atoms, for example difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.
- The term, "C1-C10-alkoxy" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached via an oxygen atom. Examples include C1-C6-alkoxy such as methoxy, ethoxy, OCH2-C2H5, OCH(CH3)2, n-butoxy, OCH(CH3)-C2H5, OCH2-CH(CH3)2, OC(CH3)3, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-methylpropoxy and the like.
- The term "C1-C10-haloalkoxy" as used herein refers to a C1-C10-alkoxy group as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, C1-C6-haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy, in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy.
- The term "C1-C6-alkoxy-C1-C6-alkyl" as used herein refers to C1-C6-alkyl which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, CH2-OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH2-OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl, 4-(1,1-dimethylethoxy)butyl and the like.
- The term "C1-C6-alkoxy-C1-C6-alkoxy" as used herein refers to C1-C6-alkoxy which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)2, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(n-propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(n-propoxy)propoxy, 3-(1-methylethoxy)propv, 3-(n-butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(n-propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(n-propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(n-propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy, 4-(1,1-dimethylethoxy)butoxy and the like.
- The term "C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkoxy" as used herein refers to C1-C4-alkoxy which is substituted by C1-C4-alkoxy-C1-C4-alkoxy as mentioned above, i.e., for example, 2-(2-methoxyethyloxy)ethyloxy, 2-(2-ethoxyethyloxy)ethyloxy;
- The term "C1-C10-alkylcarbonyl" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) bonded via the carbon atom of the carbonyl group at any bond in the alkyl group. Examples include C1-C6-alkylcarbonyl such CO-CH3, CO-C2H5, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl and the like.
- The term "C1-C10-alkoxycarbonyl" as used herein refers to a straight-chain or branched alkoxy group (as mentioned above) having 1 to 10 carbon atoms attached via the carbon atom of the carbonyl group. Examples include (C1-C6-alkoxy)carbonyl, for example CO-OCH3, CO-OC2H5, COO-CH2-C2H5, CO-OCH(CH3)2, n-butoxycarbonyl, CO-OCH(CH3)-C2H5, CO-OCH2-CH(CH3)2, CO-OC(CH3)3, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl
- The term "C1-C10-alkylthio (C1-C10-alkylsulfanyl: C1-C10-alkyl-S-)" as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached via a sulfur atom, for example C1-C4-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio.
- The term "C1-C10-alkylsulfinyl" (C1-C10-alkyl-S(=O)-), as used herein refers to a straight-chain or branched saturated hydrocarbon group (as mentioned above) having 1 to 10 carbon atoms bonded through the sulfur atom of the sulfinyl group at any bond in the alkyl group. Examples include C1-C6-alkylsulfinyl: SO-CH3, SO-C2H5, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.
- The term "C1-C10-alkylsulfonyl" (C1-C10-alkyl-S(=O)2-) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is bonded via the sulfur atom of the sulfonyl group at any bond in the alkyl group. Examples include C1-C6-alkylsulfonyl such as SO2-CH3, SO2-C2H5, n-propylsulfonyl, SO2-CH(CH3)2, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, SO2-C(CH3)3, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl and the like.
- The term "C2-C10-alkenyl" as used herein refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
- The term "C2-C10-alkynyl" as used herein refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl and the like.
- The term "C3-C10-cycloalkyl" as used herein refers to a monocyclic hydrocarbon radical having 3 to 10 carbon atoms, in particular 3 to 8 carbon atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl,
- The term "C3-C8-cycloalkyl-C1-C4-alkyl" as used herein refers to a C1-C4-alkyl which carries a C3-C8-cycloalkyl radical as defined above, for example cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl, 2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)-eth-1-yl, 1-(cyclopropylmethyl)-1-(methyl)-eth-1-yl, 1-(cyclopropylmethyl)-prop-1-yl, cyclobutylmethyl, 1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl, 2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl, 1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl, 3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl, 1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl, 1-(cyclobutylmethyl)eth-1-yl, 1-(cyclobutylmethyl)-1-(methyl)-eth-1-yl, 1-(cyclobutylmethyl)prop-1-yl, cyclopentylmethyl, 1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl, 2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl, 1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl, 3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl, 1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)-eth-1-yl, 1-(cyclopentylmethyl)-1-(methyl)-eth-1-yl, 1-(cyclopentylmethyl)-prop-1-yl, cyclohexylmethyl, 1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl, 2-cyclohexylprop-1-yl, 3-cyclohexylprop-1-yl, 1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl, 3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl, 1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl, 1-(cyclohexylmethyl)-eth-1-yl, 1-(cyclohexylmethyl)-1-(methyl)-eth-1-yl, 1-(cyclohexylmethyl)-prop-1-yl, cycloheptylmethyl, 1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl, 2-cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl, 1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl, 3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl, 1-cycloheptylbut-2-yl, 2-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl, 1-(cycloheptylmethyl)-eth-1-yl, 1-(cycloheptylmethyl)-1-(methyl)-eth-1-yl, 1-(cycloheptylmethyl)-prop-1-yl, cyclooctylmethyl, 1-cyclooctylethyl, 2-cyclooctylethyl, 1-cyclooctylprop-1-yl, 2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl, 1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl, 3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl, 1-cyclooctylbut-2-yl, 2-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl, 1-(cyclooctylmethyl)-eth-1-yl, 1-(cyclooctylmethyl)-1-(methyl)-eth-1-yl or 1-(cyclooctylmethyl)-prop-1-yl.
- The term "phenyl-C1-C4-alkyl" as used herein refers to C1-C4-alkyl which is substituted by phenyl, which may for its part be unsubstituted or carries one, two or three substituents, such as benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)-prop-1-yl, preferably benzyl, 1-phenylethyl or 2-phenylethyl and especially (R)-1-phenylethyl and (S)-1-phenylethyl.
- The term "heterocyclyl" as used herein refers to a 3- to 7-membered heterocyclic radical which has 3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of these ring members are heteroatoms selected, independently from each other, from the group consisting of oxygen, nitrogen, sulfur and a group NR5, wherein R5 has the meanings as defined above. The heterocycle may be a carbon-bonded heterocycle or may be bonded via a heteroatom. The heterocycle may be aromatic (heteroaryl) or partially or fully saturated.
- Moreover, the heterocyclyl radical may be fused to a 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring which may carry for their part one, two, three, four, five or six substituents which are selected, independently from another from the group consisting of halogen such as fluorine, chlorine, bromine and C1-C4-alkyl such as methyl.
- Examples for monocyclic heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl or isoxazolyl.
- Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothiophenyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like.
- The term "fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring" as used herein refers to a cyclic radical which carries a fused saturated C5-C7-carbocycle as defined above, a mono- or diunsaturated C5-C7-carbocycle or phenyl or to a 5-7-membered heterocyclic ring as defined above.
- Examples for C3-C10-cycloalkyl fused with a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring are indan-1-yl, indan-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl or hydrindanyl and the like.
- Examples for phenyl fused with a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring are indan-5-yl, indan-6-yl, dihydronaphthalen-5-yl, dihydronaphthalen-6-yl, 1,2,3,4-tetrahydronaphthalen-5-yl, 1,2,3,4-tetrahydronaphthalen-6-yl, quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyl, benzoxazolyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl, benzimidazolyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroisochinolinyl, chromenyl, chromanyl and the like.
- Examples for 3- to 7-membered heterocyclyl carrying a fused-on 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or a 5- to 7-membered heterocyclic ring are quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyl, benzoxazolyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl, benzimidazolyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroisochinolinyl, chromenyl, chromanyl and the like.
- As regards the pesticidal activity of the 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I, preference is given to those compounds I, in which the radical R4 is attached to the nitrogen atom of the amino group via a secondary or tertiary carbon atom. Thus, compounds I are preferred, wherein R4 is phenyl, naphthyl, C3-C10-cycloalkyl, a 3- to 7-membered heterocyclyl or a radical -A-R4a, wherein A C2-C6-alkylene which is attached to the nitrogen via a secondary or tertiary carbon atom of the C2-C6-alkylene chain. The C2-C6-alkylene chain may comprise a heteroatom selected from the group consisting of oxygen and sulfur. The compounds comprise the pure R- and S-enantiomers as well as the mixtures of the enantiomers such as the racemic mixtures. Particularly preferred among these are the pure enantiomers.
- As regards the pesticidal activity of the 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I, preference is also given to the following meaning of the radicals, in each case on their own or in combination:
- X
- is chlorine;
- R1
- is hydrogen, C1-C4-alkyl, preferably methyl, C1-C4-haloalkyl, preferably trifluoromethyl, C1-C4-alkoxy, preferably methoxy, C1-C4-alkylthio, preferably methylthio, C1-C4-alkylsulfinyl, preferably methylsulfinyl or C1-C4-alkylsulfonyl, preferably methylsulfonyl, most preferred hydrogen; however R1 may also be OH, CN, Phenoxy, Benzyloxy, C1-C4-alkoxy-C2-C4-alkoxy, C1-C4-alkoxy-C2-C4-alkoxy- C2-C4-alkoxy, (C1-C4-alkoxycarbonyl)C2-C4-alkylthio, such as 2-(methoxycarbonyl)ethylthio, 2-(ethoxycarbonyl)ethylthio, SCH2-CO-OCH3 or SCH2-CO-OCH2CH3, (hydroxycarbonyl)C2-C4-alkylthio, such as S-CH2-COOH, S-CH2CH2-COOH, (C1-C4-alkoxy)C2-C4-alkylthio such as SCH2-CH2-OCH3 or SCH2-CH2-OCH2CH3;
- R2
- is C1-C4-alkyl, preferably C1-C2-alkyl, or C1-C4-haloalkyl, preferably C1-C2-fluoroalkyl; most preferred methyl, ethyl, 2-fluoroethyl or 1-fluoroethyl;
- R3
- is hydrogen or C1-C4-alkoxy-C1-C4-alkyl, most preferred hydrogen;
- R4
- is phenyl, phenyl-C1-C4-alkyl or C3-C8-cycloalkyl, wherein each phenyl and C3-C8-cycloalkyl group may be unsubstituted or may carry one or two substituents which are selected, independently from one another, from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkoxy, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl and phenyloxy, wherein the three last-mentioned substituents for their part may be unsubstituted or may carry one or two substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen.
- A preferred embodiment of the method of the invention uses compounds of the general formula I, wherein R4 is cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl, wherein the cyclohexyl group and the phenyl group in the last three mentioned radicals may be unsubstituted or may carry one or two substituents which are selected, independently from each other, from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkoxy, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl and phenyloxy, wherein the two last mentioned substituents for their part may be unsubstituted or may carry one or two substituents which are selected independently of each other from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen.
- In an especially preferred embodiment of the method of the present invention, R4 is a cyclohexyl radical which may carry one or two substituents. One substituent is preferably attached to the 4-position of the cyclohexyl radical. Particularly preferred substituents of the radical cyclohexyl mentioned for R4 are, independently of one another, C1-C4-alkyl, especially methyl, ethyl, isopropyl, sec-butyl and tert-butyl or cyclohexyl-C1-C4-alkyl. Amongst the compounds I those are especially preferred, wherein the cyclohexyl radical carries a substituent in the 4-position, said substituent is most preferably attached cis relative to the nitrogen atom.
- In another embodiment of the method of the present invention, particular preference is given to 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines in which R4 is phenyl, benzyl, 1-phenylethyl or 2-phenylethyl which for their part carry one or two of the above defined substituents on the phenyl ring.
- The substituents are preferably selected independently of each other from the group consisting fluorine, chlorine, bromine, C1-C4-alkyl especially methyl, ethyl, n-propyl, isopropyl, 2-butyl and tert-butyl; C1-C4-alkoxy, especially methoxy, ethoxy, tert-butoxy, C1-C4-haloalkyl, especially trifluoromethyl and C1-C4-haloalkoxy, especially trifluorodifluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy. In this embodiment, compounds are especially preferred, wherein R4 is 1-phenylethyl which carries at least one substituent as defined above, especially one which has been indicated as preferred. Most preferably said substituent is attached in the 4-position of the phenyl radical. Particularly preferred among these are compounds I in which R4 is the pure enantiomer or a racemic mixture.
- In another embodiment of the method of the invention the radical R4 comprises a phenyl group such as in phenyl, benzyl and 1- or -2-phenylethyl, wherein the the phenyl ring carries at least one substituent which is selected from the group consisting of phenyl, cyclohexyl and phenoxy which for their part may be unsubstituted or may carry in the 2-, 3- or 4-position one or two substituents selected from the group consisting of C1-C4-alkyl, especially methyl, ethyl, n-propyl or isopropyl, C1-C4-alkoxy such as methoxy and halogen, especially fluorine, chlorine or bromine. Examples of substituents on the phenyl ring of phenyl, benzyl, 1-phenylethyl, or 2-phenylethyl are: 4-methylphenoxy, 4-ethylphenoxy, 4-isopropylphenoxy, 4-tert-butylphenoxy, 4-fluorophenoxy, 4-chlorophenoxy, 4-bromophenoxy, 2-methylphenoxy, 2-tert-butylphenoxy, 2-ethylphenoxy, 3-ethylphenoxy, 2-bromophenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 3-bromophenoxy, 3,4-difluorophenoxy, 3-chloro-4-fluorophenoxy, 4-bromo-3-chlorophenoxy, 4-chloro-3-fluorophenoxy, 3,4-dichlorophenoxy, 3,4-dimethlyphenoxy, 3-chloro-4-methylphenoxy, 3-methyl-4-chlorophenoxy or 3-methyl-4-bromophenoxy.
- Examples of compounds as used in the method of the invention are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula la (≡ I where X = Cl and R1 = R3 = H), where R2 and R4 together have the meanings given in one row of Table A.
Table A: No. R2 R4 A-1. CH3 4-CH3-cyclohexyl- A-2. CH3 cis-4-CH3-cyclohexyl- A-3. CH3 trans-4-CH3-cyclohexyl- A-4. CH3 4-C2H5-cyclohexyl- A-5. CH3 cis-4-C2H5-cyclohexyl- A-6. CH3 trans-4-C2H5-cyclohexyl- A-7. CH3 4-n-propyl-cyclohexyl- A-8. CH3 cis-4-n-propyl-cyclohexyl- A-9. CH3 trans-4-n-propyl-cyclohexyl- A-10. CH3 4-isopropyl-cyclohexyl- A-11. CH3 cis-4-isopropyl-cyclohexyl- A-12. CH3 trans-4-isopropyl-cyclohexyl- A-13. CH3 4-n-butylcyclohexyl- A-14. CH3 cis-4-n-butylcyclohexyl- A-15. CH3 trans-4-n-butylcyclohexyl- A-16. CH3 4-tert-butylcyclohexyl- A-17. CH3 cis-4-tert-butylcyclohexyl- A-18. CH3 trans-4-tert-butylcyclohexyl- A-19. CH3 4-(2-butyl)cyclohexyl- A-20. CH3 cis-4-(2-butyl)cyclohexyl- A-21. CH3 trans-4-(2-butyl)cyclohexyl- A-22. CH3 4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-23. CH3 cis-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-24. CH3 trans-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-25. CH3 C6H5- A-26. CH3 4-F-C6H4- A-27. CH3 4-Cl-C6H4- A-28. CH3 4-Br-C6H4- A-29. CH3 4-(C6H5)-C6H4- A-30. CH3 4-phenoxyphenyl A-31. CH3 benzyl A-32. CH3 4-CH3-C6H4-CH2- A-33. CH3 4-C2H5-C6H4-CH2- A-34. CH3 4-n-C3H7-C6H4-CH2- A-35. CH3 4-isopropyl-C6H4-CH2- A-36. CH3 4-n-C4H9-C6H4-CH2- A-37. CH3 4-isobutyl-C6H4-CH2- A-38. CH3 4-tert-buyl-C6H4CH2- A-39. CH3 4-F3C-C6H4CH2- A-40. CH3 4-methoxy-C6H4CH2- A-41. CH3 4-ethoxy-C6H4CH2- A-42. CH3 4-n-propoxy-C6H4CH2- A-43. CH3 4-isopropoxy-C6H4CH2- A-44. CH3 4-n-butoxy-C6H4CH2- A-45. CH3 4-tert-butoxy-C6H4CH2- A-46. CH3 4-F-C6H4CH2- A-47. CH3 4-Cl-C6H4CH2- A-48. CH3 4-Br-C6H4CH2- A-49. CH3 3,4-F2-C6H3CH2- A-50. CH3 3,4-Cl2-C6H3CH2- A-51. CH3 3,4-Br2-C6H3CH2- A-52. CH3 4-(4-CH3-C6H4-O)-C6H4-CH2- A-53. CH3 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-54. CH3 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-55. CH3 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-56. CH3 4-(4-n-C4H9-C6H4-O)-C6H4-CH2- A-57. CH3 4-(4-iso-C4H9-C6H4-O)-C6H4-CH2- A-58. CH3 4-(4-tert-C4H9-C6H4-O)-C6H4-CH2- A-59. CH3 4-(4-H3C-O-C6H4-O)-C6H4-CH2- A-60. CH3 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-61. CH3 4-(4-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-62. CH3 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-63. CH3 4-(4-tert-butoxy-C6H4-O)-C6H4-CH2- A-64. CH3 4-(4-Cl-C6H4-O)-C6H4-CH2- A-65. CH3 4-(4-Br-C6H4-O)-C6H4-CH2- A-66. CH3 4-(3-CH3-C6H4-O)-C6H4-CH2- A-67. CH3 4-(3-C2H5-C6H4-O)-C6H4-CH2- A-68. CH3 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-69. CH3 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-70. CH3 4-(3-n-C4H9-C6H4-O)-C6H4-CH2- A-71. CH3 4-(3-iso-C4H9-C6H4-O)-C6H4-CH2- A-72. CH3 4-(3-tert-butyl-C6H4-O)-C6H4-CH2- A-73. CH3 4-(3-H3C-O-C6H4-O)-C6H4-CH2- A-74. CH3 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-75. CH3 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-76. CH3 4-(3-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-77. CH3 4-(3-tert-butoxy-C6H4-O)-C6H4-CH2- A-78. CH3 4-(3-F-C6H4-O)-C6H4-CH2- A-79. CH3 4-(3-Cl-C6H4-O)-C6H4-CH2- A-80. CH3 4-(3-Br-C6H4-O)-C6H4-CH2- A-81. CH3 4-(2-CH3-C6H4-O)-C6H4-CH2- A-82. CH3 4-(2-C2H5-C6H4-O)-C6H4-CH2- A-83. CH3 4-(2-n-C3H7-C6H4-O)-C6H4-CH2- A-84. CH3 4-(2-iso-C3H7-C6H4-O)-C6H4-CH2- A-85. CH3 4-(2-n-C4H9-C6H4-O)-C6H4-CH2- A-86. CH3 4-(2-iso-C4H9-C6H4-O)-C6H4-CH2- A-87. CH3 4-(2-tert-butyl-C6H4-O)-C6H4-CH2- A-88. CH3 4-(2-H3C-O-C6H4-O)-C6H4-CH2- A-89. CH3 4-(2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-90. CH3 4-(2-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-91. CH3 4-(2-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-92. CH3 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-93. CH3 4-(2-F-C6H4-O)-C6H4-CH2- A-94. CH3 4-(2-Cl-C6H4-O)-C6H4-CH2- A-95. CH3 4-(2-Br-C6H4-O)-C6H4-CH2- A-96. CH3 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-97. CH3 4-(3,4-Cl2-C6H3-O)-C6H4-CH2- A-98. CH3 4-(3,4-(CH3)2-C6H3-O)-C6H4-CH2- A-99. CH3 4-(3-F-4-Cl-C6H3-O)-C6H4-CH2- A-100. CH3 4-(3-Cl-4-F-C6H3-O)-C6H4-CH2- A-101. CH3 4-(3-CH3-4-Cl-C6H3-O)-C6H4-CH2- A-102. CH3 4-(3-Cl-4-CH3-C6H3-O)-C6H4-CH2- A-103. CH3 4-(3-Cl-4-Br-C6H3-O)-C6H4-CH2- A-104. CH3 4-(3-CH3-4-Br-C6H3-O)-C6H4-CH2- A-105. CH3 (±) phenyl-CH(CH3)- A-106. CH3 (R) phenyl-CH(CH3)- A-107. CH3 (S) phenyl-CH(CH3)- A-108. CH3 (±) 4-F-phenyl-CH(CH3)- A-109. CH3 (R) 4-F-phenyl-CH(CH3)- A-110. CH3 (S) 4-F-phenyl-CH(CH3)- A-111. CH3 (±) 4-Cl-phenyl-CH(CH3)- A-112. CH3 (R) 4-Cl-phenyl-CH(CH3)- A-113. CH3 (S) 4-Cl-phenyl-CH(CH3)- A-114. CH3 (±) 4-Br-phenyl-CH(CH3)- A-115. CH3 (R) 4-Br-phenyl-CH(CH3)- A-116. CH3 (S) 4-Br-phenyl-CH(CH3)- A-117. CH3 (±) 4-Cl-2-F-phenyl-CH(CH3)- A-118. CH3 (R) 4-Cl-2-F-phenyl-CH(CH3)- A-119. CH3 (S) 4-Cl-2-F-phenyl-CH(CH3)- A-120. CH3 (±) 6-Cl-2-F-phenyl-CH(CH3)- A-121. CH3 (R) 6-Cl-2-F-phenyl-CH(CH3)- A-122. CH3 (S) 6-Cl-2-F-phenyl-CH(CH3)- A-123. CH3 (±) 2-F-phenyl-CH(CH3)- A-124. CH3 (R) 2-F-phenyl-CH(CH3)- A-125. CH3 (S) 2-F-phenyl-CH(CH3)- A-126. CH3 (S) 2,4-F2-phenyl-CH(CH3)- A-127. CH3 (±) 2,4-F2-phenyl-CH(CH3)- A-128. CH3 (R) 2,4-F2-phenyl-CH(CH3)- A-129. CH3 (S) 2,5-F2-phenyl-CH(CH3)- A-130. CH3 (±) 2,5-F2-phenyl-CH(CH3)- A-131. CH3 (R) 2,5-F2-phenyl-CH(CH3)- A-132. CH3 (S) 2,6-F2-phenyl-CH(CH3)- A-133. CH3 (±) 2,6-F2-phenyl-CH(CH3)- A-134. CH3 (R) 2,6-F2-phenyl-CH(CH3)- A-135. CH3 (±) 2-CH3O-phenyl-CH(CH3)- A-136. CH3 (R) 2-CH3O-phenyl-CH(CH3)- A-137. CH3 (S) 2-CH3O-phenyl-CH(CH3)- A-138. CH3 (±) 4-CH3O-phenyl-CH(CH3)- A-139. CH3 (R) 4-CH3O-phenyl-CH(CH3)- A-140. CH3 (S) 4-CH3O-phenyl-CH(CH3)- A-141. CH3 (±) 4-H5C2-O-phenyl-CH(CH3)- A-142. CH3 (R) 4-H5C2-O-phenyl-CH(CH3)- A-143. CH3 (S) 4-H5C2-O-phenyl-CH(CH3)- A-144. CH3 (±) 4-n-propoxy-phenyl-CH(CH3)- A-145. CH3 (R) 4-n-propoxy-phenyl-CH(CH3)- A-146. CH3 (S) 4-n-propoxy-phenyl-CH(CH3)- A-147. CH3 (±) 4-n-butoxy-phenyl-CH(CH3)- A-148. CH3 (R) 4-n-butoxyx-phenyl-CH(CH3)- A-149. CH3 (S) 4-n-butoxyphenyl-CH(CH3)- A-150. CH3 (±) 4-tert-butoxy-phenyl-CH(CH3)- A-151. CH3 (R) 4-tert-butoxyx-phenyl-CH(CH3)- A-152. CH3 (S) 4-tert-butoxyphenyl-CH(CH3)- A-153. CH3 (±) 4-CH3-phenyl-CH(CH3)- A-154. CH3 (R) 4-CH3-phenyl-CH(CH3)- A-155. CH3 (S) 4-CH3-phenyl-CH(CH3)- A-156. CH3 (±) 4-C2H5-phenyl-CH(CH3)- A-157. CH3 (R) 4-C2H5-phenyl-CH(CH3)- A-158. CH3 (S) 4-C2H5-phenyl-CH(CH3)- A-159. CH3 (±) 4-n-C3H7-phenyl-CH(CH3)- A-160. CH3 (R) 4-n-C3H7-phenyl-CH(CH3)- A-161. CH3 (S) 4-n-C3H7-phenyl-CH(CH3)- A-162. CH3 (±) 4-iso-C3H7-phenyl-CH(CH3)- A-163. CH3 (R) 4-iso-C3H7-phenyl-CH(CH3)- A-164. CH3 (S) 4-iso-C3H7-phenyl-CH(CH3)- A-165. CH3 (±) 4-n-C4H9-phenyl-CH(CH3)- A-166. CH3 (R) 4-n-C4H9-phenyl-CH(CH3)- A-167. CH3 (S) 4-n-C4H9-phenyl-CH(CH3)- A-168. CH3 (±) 4-tert-C4H9-phenyl-CH(CH3)- A-169. CH3 (R) 4-tert-C4H9-phenyl-CH(CH3)- A-170. CH3 (S) 4-tert-C4H9-phenyl-CH(CH3)- A-171. CH3 (±) 4-cycl.-C6H11-phenyl-CH(CH3)- A-172. CH3 (R) 4-cycl.-C6H11-phenyl-CH(CH3)- A-173. CH3 (S) 4-cycl.-C6H11-phenyl-CH(CH3)- A-174. CH3 (±) 4-OCF3-phenyl-CH(CH3)- A-175. CH3 (R) 4-OCF3-phenyl-CH(CH3)- A-176. CH3 (S) 4-OCF3-phenyl-CH(CH3)- A-177. CH3 (±) 4-CF3-phenyl-CH(CH3)- A-178. CH3 (R) 4-CF3-phenyl-CH(CH3)- A-179. CH3 (S) 4-CF3-phenyl-CH(CH3)- A-180. CH3 (±) 3-F-phenyl-CH(CH3)- A-181. CH3 (R) 3-F-phenyl-CH(CH3)- A-182. CH3 (S) 3-F-phenyl-CH(CH3)- A-183. CH3 (±) 3-Cl-phenyl-CH(CH3)- A-184. CH3 (R) 3-Cl-phenyl-CH(CH3)- A-185. CH3 (S) 3-Cl-phenyl-CH(CH3)- A-186. CH3 (±) 3-Br-phenyl-CH(CH3)- A-187. CH3 (R) 3-Br-phenyl-CH(CH3)- A-188. CH3 (S) 3-Br-phenyl-CH(CH3)- A-189. CH3 (±) 3-CF3-phenyl-CH(CH3)- A-190. CH3 (R) 3-CF3-phenyl-CH(CH3)- A-191. CH3 (S) 3-CF3-phenyl-CH(CH3)- A-192. CH3 (±) 3,4-F2-phenyl-CH(CH3)- A-193. CH3 (R) 3,4-F2-phenyl-CH(CH3)- A-194. CH3 (S) 3,4-F2-phenyl-CH(CH3)- A-195. CH3 (±) 3,4-Cl2-phenyl-CH(CH3)- A-196. CH3 (R) 3,4-Cl2-phenyl-CH(CH3)- A-197. CH3 (S) 3,4-Cl2-phenyl-CH(CH3)- A-198. CH3 (±) 3,4-Br2-phenyl-CH(CH3)- A-199. CH3 (R) 3,4-Br2-phenyl-CH(CH3)- A-200. CH3 (S) 3,4-Br2-phenyl-CH(CH3)- A-201. CH3 (±) 4-Difluoromethoxyphenyl-CH(CH3)- A-202. CH3 (R) 4-Difluoromethoxyphenyl-CH(CH3)- A-203. CH3 (S) 4-Difluoromethoxyphenyl-CH(CH3)- A-204. CH3 (±) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-205. CH3 (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-206. CH3 (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-207. CH3 (±) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-208. CH3 (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-209. CH3 (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-210. CH3 (±) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-211. CH3 (R) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-212. CH3 (S) (1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-213. CH3 (±) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-214. CH3 (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-215. CH3 (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-216. CH3 (±) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-217. CH3 (R) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-218. CH3 (S) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-219. CH3 (±) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-220. CH3 (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-221. CH3 (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-222. CH3 (±) (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-223. CH3 (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-224. CH3 (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-225. CH3 (±) (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-226. CH3 (R) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-227. CH3 (S) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-228. CH3 (±) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-229. CH3 (R) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-230. CH3 (S) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-231. CH3 C6H5CH2CH2- A-232. CH3 4-F-C6H4CH2CH2- A-233. CH3 4-Cl-C6H4CH2CH2- A-234. CH3 4-Br-C6H4CH2CH2- A-235. CH3 4-CH3O-C6H4CH2CH2- A-236. CH3 4-C2H5O-C6H4CH2CH2- A-237. CH3 4-n-C3H7O-C6H4CH2CH2- A-238. CH3 4-n-C4H9O-C6H4CH2CH2- A-239. CH3 4-t-C4H9O-C6H4CH2CH2- A-240. CH3 3,4-(CH3O)2-C6H4CH2CH2- A-241. CH3 4-H3C-C6H4CH2CH2- A-242. CH3 4-H3C-H2C-C6H4CH2CH2- A-243. CH3 4-H3C-H2C-H2C-C6H4CH2CH2- A-244. CH3 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-245. CH3 4-(CH3)3C-C6H4CH2CH2- A-246. CH3 4-F3CO-C6H4CH2CH2- A-247. CH3 4-F3C-C6H4CH2CH2- A-248. CH3 3-F3C-C6H4CH2CH2- A-249. CH3CH2 4-CH3-cyclohexyl- A-250. CH3CH2 cis-4-CH3-cyclohexyl- A-251. CH3CH2 trans-4-CH3-cyclohexyl- A-252. CH3CH2 4-C2H5-cyclohexyl- A-253. CH3CH2 cis-4-C2H5-cyclohexyl- A-254. CH3CH2 trans-4-C2H5-cyclohexyl- A-255. CH3CH2 4-n-propyl-cyclohexyl- A-256. CH3CH2 cis-4-n-propyl-cyclohexyl- A-257. CH3CH2 trans-4-n-propyl-cyclohexyl- A-258. CH3CH2 4-isopropyl-cyclohexyl- A-259. CH3CH2 cis-4-isopropyl-cyclohexyl- A-260. CH3CH2 trans-4-isopropyl-cyclohexyl- A-261. CH3CH2 4-n-butylcyclohexyl- A-262. CH3CH2 cis-4-n-butylcyclohexyl- A-263. CH3CH2 trans-4-n-butylcyclohexyl- A-264. CH3CH2 4-(2-butyl)cyclohexyl- A-265. CH3CH2 cis-4-(2-butyl)cyclohexyl- A-266. CH3CH2 trans-4-(2-butyl)cyclohexyl- A-267. CH3CH2 4-tert-butylcyclohexyl- A-268. CH3CH2 cis-4-tert-butylcyclohexyl- A-269. CH3CH2 trans-4-tert-butylcyclohexyl- A-270. CH3CH2 4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-271. CH3CH2 cis-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-272. CH3CH2 trans-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-273. CH3CH2 C6H5- A-274. CH3CH2 4-F-C6H4- A-275. CH3CH2 4-Cl-C6H4- A-276. CH3CH2 4-Br-C6H4- A-277. CH3CH2 4-(C6H5)-C6H4- A-278. CH3CH2 4-phenoxyphenyl A-279. CH3CH2 benzyl A-280. CH3CH2 4-CH3-C6H4-CH2- A-281. CH3CH2 4-C2H5-C6H4-CH2- A-282. CH3CH2 4-n-C3H7-C6H4-CH2- A-283. CH3CH2 4-isopropyl-C6H4-CH2- A-284. CH3CH2 4-n-C4H9-C6H4-CH2- A-285. CH3CH2 4-isobutyl-C6H4-CH2- A-286. CH3CH2 4-tert-butyl-C6H4CH2- A-287. CH3CH2 4-F3C-C6H4CH2- A-288. CH3CH2 4-methoxy-C6H4CH2- A-289. CH3CH2 4-ethoxy-C6H4CH2- A-290. CH3CH2 4-n-propoxy-C6H4CH2- A-291. CH3CH2 4-isopropoxy-C6H4CH2- A-292. CH3CH2 4-n-butoxy-C6H4CH2- A-293. CH3CH2 4-tert-butoxy-C6H4CH2- A-294. CH3CH2 4-F-C6H4CH2- A-295. CH3CH2 4-Cl-C6H4CH2- A-296. CH3CH2 4-Br-C6H4CH2- A-297. CH3CH2 3,4-F2-C6H3CH2- A-298. CH3CH2 3,4-Cl2-C6H3CH2- A-299. CH3CH2 3,4-Br2-C6H3CH2- A-300. CH3CH2 4-(4-CH3-C6H4-O)-C6H4-CH2- A-301. CH3CH2 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-302. CH3CH2 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-303. CH3CH2 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-304. CH3CH2 4-(4-n-C4H9-C6H4-O)-C6H4-CH2- A-305. CH3CH2 4-(4-iso-C4H9-C6H4-O)-C6H4-CH2- A-306. CH3CH2 4-(4-tert-C4H9-C6H4-O)-C6H4-CH2- A-307. CH3CH2 4-(4-H3C-O-C6H4-O)-C6H4-CH2- A-308. CH3CH2 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-309. CH3CH2 4-(4-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-310. CH3CH2 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-311. CH3CH2 4-(4-tert-butoxy-C6H4-O)-C6H4-CH2- A-312. CH3CH2 4-(4-Cl-C6H4-O)-C6H4-CH2- A-313. CH3CH2 4-(4-Br-C6H4-O)-C6H4-CH2- A-314. CH3CH2 4-(3-CH3-C6H4-O)-C6H4-CH2- A-315. CH3CH2 4-(3-C2H5-C6H4-O)-C6H4-CH2- A-316. CH3CH2 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-317. CH3CH2 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-318. CH3CH2 4-(3-n-C4H9-C6H4-O)-C6H4-CH2- A-319. CH3CH2 4-(3-iso-C4H9-C6H4-O)-C6H4-CH2- A-320. CH3CH2 4-(3-tert-butyl-C6H4-O)-C6H4-CH2- A-321. CH3CH2 4-(3-H3C-O-C6H4-O)-C6H4-CH2- A-322. CH3CH2 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-323. CH3CH2 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-324. CH3CH2 4-(3-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-325. CH3CH2 4-(3-tert-butoxy-C6H4-O)-C6H4-CH2- A-326. CH3CH2 4-(3-F-C6H4-O)-C6H4-CH2- A-327. CH3CH2 4-(3-Cl-C6H4-O)-C6H4-CH2- A-328. CH3CH2 4-(3-Br-C6H4-O)-C6H4-CH2- A-329. CH3CH2 4-(2-CH3-C6H4-O)-C6H4-CH2- A-330. CH3CH2 4-(2-C2H5-C6H4-O)-C6H4-CH2- A-331. CH3CH2 4-(2-n-C3H7-C6H4-O)-C6H4-CH2- A-332. CH3CH2 4-(2-iso-C3H7-C6H4-O)-C6H4-CH2- A-333. CH3CH2 4-(2-n-C4H9-C6H4-O)-C6H4-CH2- A-334. CH3CH2 4-(2-iso-C4H9-C6H4-O)-C6H4-CH2- A-335. CH3CH2 4-(2-tert-butyl-C6H4-O)-C6H4-CH2- A-336. CH3CH2 4-(2-H3C-O-C6H4-O)-C6H4-CH2- A-337. CH3CH2 4-(2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-338. CH3CH2 4-(2-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-339. CH3CH2 4-(2-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-340. CH3CH2 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-341. CH3CH2 4-(2-F-C6H4-O)-C6H4-CH2- A-342. CH3CH2 4-(2-Cl-C6H4-O)-C6H4-CH2- A-343. CH3CH2 4-(2-Br-C6H4-O)-C6H4-CH2- A-344. CH3CH2 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-345. CH3CH2 4-(3,4-Cl2-C6H3-O)-C6H4-CH2- A-346. CH3CH2 4-(3,4-(CH3)2-C6H3-O)-C6H4-CH2- A-347. CH3CH2 4-(3-F-4-Cl-C6H3-O)-C6H4-CH2- A-348. CH3CH2 4-(3-Cl-4-F-C6H3-O)-C6H4-CH2- A-349. CH3CH2 4-(3-CH3-4-Cl-C6H3-O)-C6H4-CH2- A-350. CH3CH2 4-(3-Cl-4-CH3-C6H3-O)-C6H4-CH2- A-351. CH3CH2 4-(3-Cl-4-Br-C6H3-O)-C6H4-CH2- A-352. CH3CH2 4-(3-CH3-4-Br-C6H3-O)-C6H4-CH2- A-353. CH3CH2 (±) phenyl-CH(CH3)- A-354. CH3CH2 (R) phenyl-CH(CH3)- A-355. CH3CH2 (S) phenyl-CH(CH3)- A-356. CH3CH2 (±) 4-F-phenyl-CH(CH3)- A-357. CH3CH2 (R) 4-F-phenyl-CH(CH3)- A-358. CH3CH2 (S) 4-F-phenyl-CH(CH3)- A-359. CH3CH2 (±) 4-Cl-phenyl-CH(CH3)- A-360. CH3CH2 (R) 4-Cl-phenyl-CH(CH3)- A-361. CH3CH2 (S) 4-Cl-phenyl-CH(CH3)- A-362. CH3CH2 (±) 4-Br-phenyl-CH(CH3)- A-363. CH3CH2 (R) 4-Br-phenyl-CH(CH3)- A-364. CH3CH2 (S) 4-Br-phenyl-CH(CH3)- A-365. CH3CH2 (±) 4-Cl-2-F-phenyl-CH(CH3)- A-366. CH3CH2 (R) 4-Cl-2-F-phenyl-CH(CH3)- A-367. CH3CH2 (S) 4-Cl-2-F-phenyl-CH(CH3)- A-368. CH3CH2 (±) 6-Cl-2-F-phenyl-CH(CH3)- A-369. CH3CH2 (R) 6-Cl-2-F-phenyl-CH(CH3)- A-370. CH3CH2 (S) 6-Cl-2-F-phenyl-CH(CH3)- A-371. CH3CH2 (±) 2-F-phenyl-CH(CH3)- A-372. CH3CH2 (R) 2-F-phenyl-CH(CH3)- A-373. CH3CH2 (S) 2-F-phenyl-CH(CH3)- A-374. CH3CH2 (S) 2,4-F2-phenyl-CH(CH3)- A-375. CH3CH2 (±) 2,4-F2-phenyl-CH(CH3)- A-376. CH3CH2 (R) 2,4-F2-phenyl-CH(CH3)- A-377. CH3CH2 (S) 2,5-F2-phenyl-CH(CH3)- A-378. CH3CH2 (±) 2,5-F2-phenyl-CH(CH3)- A-379. CH3CH2 (R) 2,5-F2-phenyl-CH(CH3)- A-380. CH3CH2 (S) 2,6-F2-phenyl-CH(CH3)- A-381. CH3CH2 (±) 2,6-F2-phenyl-CH(CH3)- A-382. CH3CH2 (R) 2,6-F2-phenyl-CH(CH3)- A-383. CH3CH2 (±) 2-CH3O-phenyl-CH(CH3)- A-384. CH3CH2 (R) 2-CH3O-phenyl-CH(CH3)- A-385. CH3CH2 (S) 2-CH3O-phenyl-CH(CH3)- A-386. CH3CH2 (±) 4-CH3O-phenyl-CH(CH3)- A-387. CH3CH2 (R) 4-CH3O-phenyl-CH(CH3)- A-388. CH3CH2 (S) 4-CH3O-phenyl-CH(CH3)- A-389. CH3CH2 (±) 4-H5C2-O-phenyl-CH(CH3)- A-390. CH3CH2 (R) 4-H5C2-O-phenyl-CH(CH3)- A-391. CH3CH2 (S) 4-H5C2-O-phenyl-CH(CH3)- A-392. CH3CH2 (±) 4-n-propoxy-phenyl-CH(CH3)- A-393. CH3CH2 (R) 4-n-propoxy-phenyl-CH(CH3)- A-394. CH3CH2 (S) 4-n-propoxy-phenyl-CH(CH3)- A-395. CH3CH2 (±) 4-n-butoxy-phenyl-CH(CH3)- A-396. CH3CH2 (R) 4-n-butoxyx-phenyl-CH(CH3)- A-397. CH3CH2 (S) 4-n-butoxyphenyl-CH(CH3)- A-398. CH3CH2 (±) 4-tert-butoxy-phenyl-CH(CH3)- A-399. CH3CH2 (R) 4-tert-butoxyx-phenyl-CH(CH3)- A-400. CH3CH2 (S) 4-tert-butoxyphenyl-CH(CH3)- A-401. CH3CH2 (±) 4-CH3-phenyl-CH(CH3)- A-402. CH3CH2 (R) 4-CH3-phenyl-CH(CH3)- A-403. CH3CH2 (S) 4-CH3-phenyl-CH(CH3)- A-404. CH3CH2 (±) 4-C2H5-phenyl-CH(CH3)- A-405. CH3CH2 (R) 4-C2H5-phenyl-CH(CH3)- A-406. CH3CH2 (S) 4-C2H5-phenyl-CH(CH3)- A-407. CH3CH2 (±) 4-n-C3H7-phenyl-CH(CH3)- A-408. CH3CH2 (R) 4-n-C3H7-phenyl-CH(CH3)- A-409. CH3CH2 (S) 4-n-C3H7-phenyl-CH(CH3)- A-410. CH3CH2 (±) 4-iso-C3H7-phenyl-CH(CH3)- A-411. CH3CH2 (R) 4-iso-C3H7-phenyl-CH(CH3)- A-412. CH3CH2 (S) 4-iso-C3H7-phenyl-CH(CH3)- A-413. CH3CH2 (±) 4-n-C4H9-phenyl-CH(CH3)- A-414. CH3CH2 (R) 4-n-C4H9-phenyl-CH(CH3)- A-415. CH3CH2 (S) 4-n-C4H9-phenyl-CH(CH3)- A-416. CH3CH2 (±) 4-tert-C4H9-phenyl-CH(CH3)- A-417. CH3CH2 (R) 4-tert-C4H9-phenyl-CH(CH3)- A-418. CH3CH2 (S) 4-tert-C4H9-phenyl-CH(CH3)- A-419. CH3CH2 (±) 4-cycl.-C6H11-phenyl-CH(CH3)- A-420. CH3CH2 (R) 4-cycl.-C6H11-phenyl-CH(CH3)- A-421. CH3CH2 (S) 4-cycl.-C6H11-phenyl-CH(CH3)- A-422. CH3CH2 (±) 4-OCF3-phenyl-CH(CH3)- A-423. CH3CH2 (R) 4-OCF3-phenyl-CH(CH3)- A-424. CH3CH2 (S) 4-OCF3-phenyl-CH(CH3)- A-425. CH3CH2 (±) 4-CF3-phenyl-CH(CH3)- A-426. CH3CH2 (R) 4-CF3-phenyl-CH(CH3)- A-427. CH3CH2 (S) 4-CF3-phenyl-CH(CH3)- A-428. CH3CH2 (±) 3-F-phenyl-CH(CH3)- A-429. CH3CH2 (R) 3-F-phenyl-CH(CH3)- A-430. CH3CH2 (S) 3-F-phenyl-CH(CH3)- A-431. CH3CH2 (±) 3-Cl-phenyl-CH(CH3)- A-432. CH3CH2 (R) 3-Cl-phenyl-CH(CH3)- A-433. CH3CH2 (S) 3-Cl-phenyl-CH(CH3)- A-434. CH3CH2 (±) 3-Br-phenyl-CH(CH3)- A-435. CH3CH2 (R) 3-Br-phenyl-CH(CH3)- A-436. CH3CH2 (S) 3-Br-phenyl-CH(CH3)- A-437. CH3CH2 (±) 3-CF3-phenyl-CH(CH3)- A-438. CH3CH2 (R) 3-CF3-phenyl-CH(CH3)- A-439. CH3CH2 (S) 3-CF3-phenyl-CH(CH3)- A-440. CH3CH2 (±) 3,4-F2-phenyl-CH(CH3)- A-441. CH3CH2 (R) 3,4-F2-phenyl-CH(CH3)- A-442. CH3CH2 (S) 3,4-F2-phenyl-CH(CH3)- A-443. CH3CH2 (±) 3,4-Cl2-phenyl-CH(CH3)- A-444. CH3CH2 (R) 3,4-Cl2-phenyl-CH(CH3)- A-445. CH3CH2 (S) 3,4-Cl2-phenyl-CH(CH3)- A-446. CH3CH2 (±) 3,4-Br2-phenyl-CH(CH3)- A-447. CH3CH2 (R) 3,4-Br2-phenyl-CH(CH3)- A-448. CH3CH2 (S) 3,4-Br2-phenyl-CH(CH3)- A-449. CH3CH2 (±) 4-Difluoromethoxyphenyl-CH(CH3)- A-450. CH3CH2 (R) 4-Difluoromethoxyphenyl-CH(CH3)- A-451. CH3CH2 (S) 4-Difluoromethoxyphenyl-CH(CH3)- A-452. CH3CH2 (±) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-453. CH3CH2 (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-454. CH3CH2 (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-455. CH3CH2 (±) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-456. CH3CH2 (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-457. CH3CH2 (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-458. CH3CH2 (±) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-459. CH3CH2 (R) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-460. CH3CH2 (S) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-461. CH3CH2 (±) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-462. CH3CH2 (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-463. CH3CH2 (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-464. CH3CH2 (±) (1,1,4,4,7-pentamethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-465. CH3CH2 (R) (1,1,4,4,7-pentamethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-466. CH3CH2 (S) (1,1,4,4,7-pentamethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-467. CH3CH2 (±) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-468. CH3CH2 (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin- 6-yl)-CH(CH3)- A-469. CH3CH2 (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin- 6-yl)-CH(CH3)- A-470. CH3CH2 (±) (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-471. CH3CH2 (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-472. CH3CH2 (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-473. CH3CH2 (±) (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-474. CH3CH2 (R) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-475. CH3CH2 (S) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-476. CH3CH2 (±) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-477. CH3CH2 (R) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-478. CH3CH2 (S) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-479. CH3CH2 C6H5CH2CH2- A-480. CH3CH2 4-F-C6H4CH2CH2- A-481. CH3CH2 4-Cl-C6H4CH2CH2- A-482. CH3CH2 4-Br-C6H4CH2CH2- A-483. CH3CH2 4-CH3O-C6H4CH2CH2- A-484. CH3CH2 4-C2H5O-C6H4CH2CH2- A-485. CH3CH2 4-n-C3H7O-C6H4CH2CH2- A-486. CH3CH2 4-n-C4H9O-C6H4CH2CH2- A-487. CH3CH2 4-t-C4H9O-C6H4CH2CH2- A-488. CH3CH2 3,4-(CH3O)2-C6H4CH2CH2- A-489. CH3CH2 4-H3C-C6H4CH2CH2- A-490. CH3CH2 4-H3C-H2C-C6H4CH2CH2- A-491. CH3CH2 4-H3C-H2C-H2C-C6H4CH2CH2- A-492. CH3CH2 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-493. CH3CH2 4-(CH3)3C-C6H4CH2CH2- A-494. CH3CH2 4-F3CO-C6H4CH2CH2- A-495. CH3CH2 4-F3C-C6H4CH2CH2- A-496. CH3CH2 3-F3C-C6H4CH2CH2- A-497. CH3CHF 4-CH3-cyclohexyl- A-498. CH3CHF cis-4-CH3-cyclohexyl- A-499. CH3CHF trans-4-CH3-cyclohexyl- A-500. CH3CHF 4-C2H5-cyclohexyl- A-501. CH3CHF cis-4-C2H5-cyclohexyl- A-502. CH3CHF trans-4-C2H5-cyclohexyl- A-503. CH3CHF 4-n-propyl-cyclohexyl- A-504. CH3CHF cis-4-n-propyl-cyclohexyl- A-505. CH3CHF trans-4-n-propyl-cyclohexyl- A-506. CH3CHF 4-isopropyl-cyclohexyl- A-507. CH3CHF cis-4-isopropyl-cyclohexyl- A-508. CH3CHF trans-4-isopropyl-cyclohexyl- A-509. CH3CHF 4-n-butylcyclohexyl- A-510. CH3CHF cis-4-n-butylcyclohexyl- A-511. CH3CHF trans-4-n-butylcyclohexyl- A-512. CH3CHF 4-tert-butylcyclohexyl- A-513. CH3CHF cis-4-tert-butylcyclohexyl- A-514. CH3CHF trans-4-tert-butylcyclohexyl- A-515. CH3CHF 4-(2-butyl)cyclohexyl- A-516. CH3CHF cis-4-(2-butyl)cyclohexyl- A-517. CH3CHF trans-4-(2-butyl)cyclohexyl- A-518. CH3CHF 4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-519. CH3CHF cis-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-520. CH3CHF trans-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-521. CH3CHF C6H5- A-522. CH3CHF 4-F-C6H4- A-523. CH3CHF 4-Cl-C6H4- A-524. CH3CHF 4-Br-C6H4- A-525. CH3CHF 4-(C6H5)-C6H4- A-526. CH3CHF 4-phenoxyphenyl A-527. CH3CHF benzyl A-528. CH3CHF 4-CH3-C6H4-CH2- A-529. CH3CHF 4-C2H5-C6H4-CH2- A-530. CH3CHF 4-n-C3H7-C6H4-CH2- A-531. CH3CHF 4-isopropyl-C6H4-CH2- A-532. CH3CHF 4-n-C4H9-C6H4-CH2- A-533. CH3CHF 4-isobutyl-C6H4-CH2- A-534. CH3CHF 4-tert-buyl-C6H4CH2- A-535. CH3CHF 4-F3C-C6H4CH2- A-536. CH3CHF 4-methoxy-C6H4CH2- A-537. CH3CHF 4-ethoxy-C6H4CH2- A-538. CH3CHF 4-n-propoxy-C6H4CH2- A-539. CH3CHF 4-isopropoxy-C6H4CH2- A-540. CH3CHF 4-n-butoxy-C6H4CH2- A-541. CH3CHF 4-tert-butoxy-C6H4CH2- A-542. CH3CHF 4-F-C6H4CH2- A-543. CH3CHF 4-Cl-C6H4CH2- A-544. CH3CHF 4-Br-C6H4CH2- A-545. CH3CHF 3,4-F2-C6H3CH2- A-546. CH3CHF 3,4-Cl2-C6H3CH2- A-547. CH3CHF 3,4-Br2-C6H3CH2- A-548. CH3CHF 4-(4-CH3-C6H4-O)-C6H4-CH2- A-549. CH3CHF 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-550. CH3CHF 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-551. CH3CHF 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-552. CH3CHF 4-(4-n-C4H9-C6H4-O)-C6H4-CH2- A-553. CH3CHF 4-(4-iso-C4H9-C6H4-O)-C6H4-CH2- A-554. CH3CHF 4-(4-tert-C4H9-C6H4-O)-C6H4-CH2- A-555. CH3CHF 4-(4-H3C-O-C6H4-O)-C6H4-CH2- A-556. CH3CHF 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-557. CH3CHF 4-(4-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-558. CH3CHF 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-559. CH3CHF 4-(4-tert-butoxy-C6H4-O)-C6H4-CH2- A-560. CH3CHF 4-(4-Cl-C6H4-O)-C6H4-CH2- A-561. CH3CHF 4-(4-Br-C6H4-O)-C6H4-CH2- A-562. CH3CHF 4-(3-CH3-C6H4-O)-C6H4-CH2- A-563. CH3CHF 4-(3-C2H5-C6H4-O)-C6H4-CH2- A-564. CH3CHF 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-565. CH3CHF 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-566. CH3CHF 4-(3-n-C4H9-C6H4-O)-C6H4-CH2- A-567. CH3CHF 4-(3-iso-C4H9-C6H4-O)-C6H4-CH2- A-568. CH3CHF 4-(3-tert-butyl-C6H4-O)-C6H4-CH2- A-569. CH3CHF 4-(3-H3C-O-C6H4-O)-C6H4-CH2- A-570. CH3CHF 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-571. CH3CHF 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-572. CH3CHF 4-(3-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-573. CH3CHF 4-(3-tert-butoxy-C6H4-O)-C6H4-CH2- A-574. CH3CHF 4-(3-F-C6H4-O)-C6H4-CH2- A-575. CH3CHF 4-(3-Cl-C6H4-O)-C6H4-CH2- A-576. CH3CHF 4-(3-Br-C6H4-O)-C6H4-CH2- A-577. CH3CHF 4-(2-CH3-C6H4-O)-C6H4-CH2- A-578. CH3CHF 4-(2-C2H5-C6H4-O)-C6H4-CH2- A-579. CH3CHF 4-(2-n-C3H7-C6H4-O)-C6H4-CH2- A-580. CH3CHF 4-(2-iso-C3H7-C6H4-O)-C6H4-CH2- A-581. CH3CHF 4-(2-n-C4H9-C6H4-O)-C6H4-CH2- A-582. CH3CHF 4-(2-iso-C4H9-C6H4-O)-C6H4-CH2- A-583. CH3CHF 4-(2-tert-butyl-C6H4-O)-C6H4-CH2- A-584. CH3CHF 4-(2-H3C-O-C6H4-O)-C6H4-CH2- A-585. CH3CHF 4-(2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-586. CH3CHF 4-(2-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-587. CH3CHF 4-(2-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-588. CH3CHF 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-589. CH3CHF 4-(2-F-C6H4-O)-C6H4-CH2- A-590. CH3CHF 4-(2-Cl-C6H4-O)-C6H4-CH2- A-591. CH3CHF 4-(2-Br-C6H4-O)-C6H4-CH2- A-592. CH3CHF 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-593. CH3CHF 4-(3,4-Cl2-C6H3-O)-C6H4-CH2- A-594. CH3CHF 4-(3,4-(CH3)2-C6H3-O)-C6H4-CH2- A-595. CH3CHF 4-(3-F-4-Cl-C6H3-O)-C6H4-CH2- A-596. CH3CHF 4-(3-Cl-4-F-C6H3-O)-C6H4-CH2- A-597. CH3CHF 4-(3-CH3-4-Cl-C6H3-O)-C6H4-CH2- A-598. CH3CHF 4-(3-Cl-4-CH3-C6H3-O)-C6H4-CH2- A-599. CH3CHF 4-(3-Cl-4-Br-C6H3-O)-C6H4-CH2- A-600. CH3CHF 4-(3-CH3-4-Br-C6H3-O)-C6H4-CH2- A-601. CH3CHF (±) phenyl-CH(CH3)- A-602. CH3CHF (R) phenyl-CH(CH3)- A-603. CH3CHF (S) phenyl-CH(CH3)- A-604. CH3CHF (±) 4-F-phenyl-CH(CH3)- A-605. CH3CHF (R) 4-F-phenyl-CH(CH3)- A-606. CH3CHF (S) 4-F-phenyl-CH(CH3)- A-607. CH3CHF (±) 4-Cl-phenyl-CH(CH3)- A-608. CH3CHF (R) 4-Cl-phenyl-CH(CH3)- A-609. CH3CHF (S) 4-Cl-phenyl-CH(CH3)- A-610. CH3CHF (±) 4-Br-phenyl-CH(CH3)- A-611. CH3CHF (R) 4-Br-phenyl-CH(CH3)- A-612. CH3CHF (S) 4-Br-phenyl-CH(CH3)- A-613. CH3CHF (±) 4-Cl-2-F-phenyl-CH(CH3)- A-614. CH3CHF (R) 4-Cl-2-F-phenyl-CH(CH3)- A-615. CH3CHF (S) 4-Cl-2-F-phenyl-CH(CH3)- A-616. CH3CHF (±) 6-Cl-2-F-phenyl-CH(CH3)- A-617. CH3CHF (R) 6-Cl-2-F-phenyl-CH(CH3)- A-618. CH3CHF (S) 6-Cl-2-F-phenyl-CH(CH3)- A-619. CH3CHF (±) 2-F-phenyl-CH(CH3)- A-620. CH3CHF (R) 2-F-phenyl-CH(CH3)- A-621. CH3CHF (S) 2-F-phenyl-CH(CH3)- A-622. CH3CHF (S) 2,4-F2-phenyl-CH(CH3)- A-623. CH3CHF (±) 2,4-F2-phenyl-CH(CH3)- A-624. CH3CHF (R) 2,4-F2-phenyl-CH(CH3)- A-625. CH3CHF (S) 2,5-F2-phenyl-CH(CH3)- A-626. CH3CHF (±) 2,5-F2-phenyl-CH(CH3)- A-627. CH3CHF (R) 2,5-F2-phenyl-CH(CH3)- A-628. CH3CHF (S) 2,6-F2-phenyl-CH(CH3)- A-629. CH3CHF (±) 2,6-F2-phenyl-CH(CH3)- A-630. CH3CHF (R) 2,6-F2-phenyl-CH(CH3)- A-631. CH3CHF (±) 2-CH3O-phenyl-CH(CH3)- A-632. CH3CHF (R) 2-CH3O-phenyl-CH(CH3)- A-633. CH3CHF (S) 2-CH3O-phenyl-CH(CH3)- A-634. CH3CHF (±) 4-CH3O-phenyl-CH(CH3)- A-635. CH3CHF (R) 4-CH3O-phenyl-CH(CH3)- A-636. CH3CHF (S) 4-CH3O-phenyl-CH(CH3)- A-637. CH3CHF (±) 4-H5C2-O-phenyl-CH(CH3)- A-638. CH3CHF (R) 4-H5C2-O-phenyl-CH(CH3)- A-639. CH3CHF (S) 4-H5C2-O-phenyl-CH(CH3)- A-640. CH3CHF (±) 4-n-propoxy-phenyl-CH(CH3)- A-641. CH3CHF (R) 4-n-propoxy-phenyl-CH(CH3)- A-642. CH3CHF (S) 4-n-propoxy-phenyl-CH(CH3)- A-643. CH3CHF (±) 4-n-butoxy-phenyl-CH(CH3)- A-644. CH3CHF (R) 4-n-butoxyx-phenyl-CH(CH3)- A-645. CH3CHF (S) 4-n-butoxyphenyl-CH(CH3)- A-646. CH3CHF (±) 4-tert-butoxy-phenyl-CH(CH3)- A-647. CH3CHF (R) 4-tert-butoxyx-phenyl-CH(CH3)- A-648. CH3CHF (S) 4-tert-butoxyphenyl-CH(CH3)- A-649. CH3CHF (±) 4-CH3-phenyl-CH(CH3)- A-650. CH3CHF (R) 4-CH3-phenyl-CH(CH3)- A-651. CH3CHF (S) 4-CH3-phenyl-CH(CH3)- A-652. CH3CHF (±) 4-C2H5-phenyl-CH(CH3)- A-653. CH3CHF (R) 4-C2H5-phenyl-CH(CH3)- A-654. CH3CHF (S) 4-C2H5-phenyl-CH(CH3)- A-655. CH3CHF (±) 4-n-C3H7-phenyl-CH(CH3)- A-656. CH3CHF (R) 4-n-C3H7-phenyl-CH(CH3)- A-657. CH3CHF (S) 4-n-C3H7-phenyl-CH(CH3)- A-658. CH3CHF (±) 4-iso-C3H7-phenyl-CH(CH3)- A-659. CH3CHF (R) 4-iso-C3H7-phenyl-CH(CH3)- A-660. CH3CHF (S) 4-iso-C3H7-phenyl-CH(CH3)- A-661. CH3CHF (±) 4-n-C4H9-phenyl-CH(CH3)- A-662. CH3CHF (R) 4-n-C4H9-phenyl-CH(CH3)- A-663. CH3CHF (S) 4-n-C4H9-phenyl-CH(CH3)- A-664. CH3CHF (±) 4-tert-C4H9-phenyl-CH(CH3)- A-665. CH3CHF (R) 4-tert-C4H9-phenyl-CH(CH3)- A-666. CH3CHF (S) 4-tert-C4H9-phenyl-CH(CH3)- A-667. CH3CHF (±) 4-cycl.-C6H11-phenyl-CH(CH3)- A-668. CH3CHF (R) 4-cycl.-C6H11-phenyl-CH(CH3)- A-669. CH3CHF (S) 4-cycl.-C6H11-phenyl-CH(CH3)- A-670. CH3CHF (±) 4-OCF3-phenyl-CH(CH3)- A-671. CH3CHF (R) 4-OCF3-phenyl-CH(CH3)- A-672. CH3CHF (S) 4-OCF3-phenyl-CH(CH3)- A-673. CH3CHF (±) 4-CF3-phenyl-CH(CH3)- A-674. CH3CHF (R) 4-CF3-phenyl-CH(CH3)- A-675. CH3CHF (S) 4-CF3-phenyl-CH(CH3)- A-676. CH3CHF (±) 3-F-phenyl-CH(CH3)- A-677. CH3CHF (R) 3-F-phenyl-CH(CH3)- A-678. CH3CHF (S) 3-F-phenyl-CH(CH3)- A-679. CH3CHF (±) 3-Cl-phenyl-CH(CH3)- A-680. CH3CHF (R) 3-Cl-phenyl-CH(CH3)- A-681. CH3CHF (S) 3-Cl-phenyl-CH(CH3)- A-682. CH3CHF (±) 3-Br-phenyl-CH(CH3)- A-683. CH3CHF (R) 3-Br-phenyl-CH(CH3)- A-684. CH3CHF (S) 3-Br-phenyl-CH(CH3)- A-685. CH3CHF (±) 3-CF3-phenyl-CH(CH3)- A-686. CH3CHF (R) 3-CF3-phenyl-CH(CH3)- A-687. CH3CHF (S) 3-CF3-phenyl-CH(CH3)- A-688. CH3CHF (±) 3,4-F2-phenyl-CH(CH3)- A-689. CH3CHF (R) 3,4-F2-phenyl-CH(CH3)- A-690. CH3CHF (S) 3,4-F2-phenyl-CH(CH3)- A-691. CH3CHF (±) 3,4-Cl2-phenyl-CH(CH3)- A-692. CH3CHF (R) 3,4-Cl2-phenyl-CH(CH3)- A-693. CH3CHF (S) 3,4-Cl2-phenyl-CH(CH3)- A-694. CH3CHF (±) 3,4-Br2-phenyl-CH(CH3)- A-695. CH3CHF (R) 3,4-Br2-phenyl-CH(CH3)- A-696. CH3CHF (S) 3,4-Br2-phenyl-CH(CH3)- A-697. CH3CHF (±) 4-Difluoromethoxyphenyl-CH(CH3)- A-698. CH3CHF (R) 4-Difluoromethoxyphenyl-CH(CH3)- A-699. CH3CHF (S) 4-Difluoromethoxyphenyl-CH(CH3)- A-700. CH3CHF (±) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-701. CH3CHF (R) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-702. CH3CHF (S) 4-(1,1,2,2-tetrafluoroethoxy)phenyl-CH(CH3)- A-703. CH3CHF (±) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-704. CH3CHF (R) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-705. CH3CHF (S) (5,5,7,7-tetramethylindan-2-yl)-CH(CH3)- A-706. CH3CHF (±) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-707. CH3CHF (R) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-708. CH3CHF (S) (1,1,4,4,-tetramethyl-1,2,3,4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-709. CH3CHF (±) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-710. CH3CHF (R) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-711. CH3CHF (S) (1,1-dimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-712. CH3CHF (±) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-713. CH3CHF (R) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-714. CH3CHF (S) (1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-715. CH3CHF (±) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-716. CH3CHF (R) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-717. CH3CHF (S) (1,1,7-trimethyl-1,2,3,4-tetrahydronaphthalin-6-yl)-CH(CH3)- A-718. CH3CHF (±)(2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-719. CH3CHF (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-720. CH3CHF (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-721. CH3CHF (±) (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-722. CH3CHF (R) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-723. CH3CHF (S) 2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-724. CH3CHF (±) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-725. CH3CHF (R) (2,2-difluorobenzodioxole-6-yl)CH(C2H5)- A-726. CH3CHF (S) (2,2-difluorobenzodioxole-5-yl)CH(C2H5)- A-727. CH3CHF C6H5CH2CH2- A-728. CH3CHF 4-F-C6H4CH2CH2- A-729. CH3CHF 4-Cl-C6H4CH2CH2- A-730. CH3CHF 4-Br-C6H4CH2CH2- A-731. CH3CHF 4-CH3O-C6H4CH2CH2- A-732. CH3CHF 4-C2H5O-C6H4CH2CH2- A-733. CH3CHF 4-n-C3H7O-C6H4CH2CH2- A-734. CH3CHF 4-n-C4H9O-C6H4CH2CH2- A-735. CH3CHF 4-t-C4H9O-C6H4CH2CH2- A-736. CH3CHF 3,4-(CH3O)2-C6H4CH2CH2- A-737. CH3CHF 4-H3C-C6H4CH2CH2- A-738. CH3CHF 4-H3C-H2C-C6H4CH2CH2- A-739. CH3CHF 4-H3C-H2C-H2C-C6H4CH2CH2- A-740. CH3CHF 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-741. CH3CHF 4-(CH3)3C-C6H4CH2CH2- A-742. CH3CHF 4-F3CO-C6H4CH2CH2- A-743. CH3CHF 4-F3C-C6H4CH2CH2- A-744. CH3CHF 3-F3C-C6H4CH2CH2- - Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula Ib, where X is Cl, R1 is CH3 and R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula Ic, where X is Cl, R1 is OCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula , where X is Cl, R1 is SCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is SOCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is SO2CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is CF3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is CN, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OH, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCHF2, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCF2CHF2, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCF3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCH2C6H5, R3 is H, R2 and R4 together have the mean-ings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCH2CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCH2C≡CH, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is OCH(CH3)2, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is O-CH2CH2-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compound as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is O-CH2CH2-O-CH2CH2-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is S-CH2CH2-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is S-CH2C(O)-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is S-CH2CH2C(O)-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
- Examples of compounds as used in the method of the invention also are the 6-chloro-[1,2,4]triazolo-[1,5-a]pyrimidines of the formula I, where X is Cl, R1 is S-CH2C(O)-OH, R3 is H, R2 and R4 together have the meanings given in one row of Table A.
-
- In Scheme 1, the variables R1, R2, R3, R4 and X are as defined above. The reaction of a 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine of the formula II with an amine of the formula III may be carried out in the presence or absence of a solvent. Suitable solvents are all solvents which are inert under the reaction conditions, such as aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, petrol ether, cyclohexane, benzene, toluene, xylenes, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, cyclic ethers, such as tetrahydrofuran or dioxane, halogenated hydrocarbons such as dichloromethane or trichloromethane or C1-C4-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol or tert-butanol, water or mixtures of these solvents. It is preferred that the reaction is carried out in the presence of a solvent. If the reaction is carried out in the absence of a solvent, the amine (III) is employed in a large excess, based on 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidin II.
- It is also preferred that the reaction is carried out in the presence of a base. Suitable bases include organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, 2,3-lutidine, 2,4-lutidine or 2,5-lutidine and inorganic bases, for example alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and sodium carbonate, calcium carbonate and alkali metal hydrogencarbonates such as sodium hydrogen carbonate. An excess of the amine III may serve as base.
- The reaction temperature is usually in the range of from 0°C to the boiling of the solvent, preferably of from 20 to the 120°C.
- The molar ratio of amine III to 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II is generally at least 0.9:1, preferably at least 1:1. It may be advantageous to employ the amine III in a slight excess, for example of up to 20%, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II.
- In general, the base is employed in at least equimolar amount to a 2-fold molar excess, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II. It may be advantageous to employ the base in a slight excess, for example up to 30%, based on the 6,7-dihalogeno-[1,2,4]triazolo-[1,5-a]pyrimidine II.
- The reaction mixtures are worked up in a customary manner, for example by adding diluted acids, for example mineral acids such as diluted hydrochloric acid, hydrobromic acid and sulfuric acid or aqueous organic acids such as trifluoroacetic acid or acetic acid, aqueous hydrochloric acid being preferred, phase separation and, if appropriate, chromatographic purification, recrystallization, trituration or digestion. The compounds according to the present invention are in general oils, resinous compounds or predominantly crystalline solid materials.
- From the preparation, the compounds of formula I may be obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.
- Some of the amines of the formula III which are employed as starting materials are commercially available. Other may be prepared by processes known in the art, for example, by conversion of the corresponding alcohols into its tosylates which are then converted to the phthalimido derivatives. The phthalimido derivatives are converted to the desired amines by using hydrazine or any other suitable cleavage agent using conventional methods [e.g. J. Am. Soc., Vol. 117, p. 7025 (1995);
WO 93/20804 -
- In Scheme 2, the variables R1, R2 and X are as defined above, X' is halogen, R is alkyl, preferably C1-C6-alkyl, in particular methyl or ethyl and Hal means a halogenating agent. In the first step the 5-aminotriazole of the general formula IV is reacted with the malonic ester of the general formula V. The reaction may be carried out under alkaline conditions, preferably using high boiling tertiary amines as for example tri-n-butylamine. The 5-aminotriazoles IV are commercially available or can be prepared in analogy to the methods which are well known in the art.
- In the second step of Scheme 2 the resulting 6-halogeno-7-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine of the general formula VI is treated with a halogenating agent, preferably with a brominating or chlorinating agent. Suitable halogenating agents include inorganic acid halides, preferably acid chlorides or acide bromides such as thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosphorus pentachloride or phosphorus tribromide, phosphorus trichloride and mixtures of these. If phosphorus oxychloride is used as a halogenating agent, the reaction is preferably carried out in the presence of a mineral acid, such as polyphosphoric acid and pyridinium salts such as pyridinium bromide or chloride. Preferred halogenating agents are POCl3, PCl3/Cl2 or PCl5 and mixtures of these. The reaction can be carried out in the presence or absence of a solvent. The acid halides thionylchloride, phoshorus trichloride or phosphoryl chloride may simultaneous act as solvent. Suitable solvents are furthermore acetonitrile or dichloromethane. The halogenating agent is generally used in at least equimolar amounts, based on the 6-halogeno-7-hydroxy-[1,2,4]triazolo[1,5-a]pyrimidine of the general formula VI. The reaction is suitable carried out at a temperature in the range from 0°C to 150°C, the preferred reaction temperature being from 80°C to 125°C.
- Due to their excellent activity, the compounds of the general formula I may be used for controlling animal pests. Animal pests include harmful insects, acaridae and arachnids Accordingly, the invention further provides agriculturally composition for combating animal pests, especially insects, arachnids and/or acaridae which comprises such amount of at least one compound of the general formula I' as defined in claim 17 or at least an agriculturally useful salt of I' as defined in claim 17 and a least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant.
- Such a composition may contain a single active compound of the general formula I or a mixture of several active compounds I according to the present invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers.
- The 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines and the pestidicidal compositions comprising them are effective agents for controlling animal pests. Animal pests controlled by the compounds of formula I include for example:
- insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;
- beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;
- dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;
- thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;
- hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;
- heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,
- homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;
- termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus und Termes natalensis;
- orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;
- Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis;
- Siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp.
- The compounds of the formula I are preferably used for controlling pests of the orders Lepidoptera, Coleoptera, Homoptera and Acarina.
- The compounds of formula (I) or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula (I). The term "crop" refers both to growing and harvested crops.
- The animal pest, especially the insect, acaridae, arachnid, plant and/or soil or water in which the plant is growing can be contacted with the present compound(s) I or composition(s) containing them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest, especially the insect, acaridae and/or arachnid, and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest, especially the insect, acaridae, and/or arachnid, and/or plant).
- Moreover, animal pests, especially insects, acaridae or arachnids may be controlled by contacting the target pest, its food supply or its locus with a pesticidally effective amount of compounds of formula (I). As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
- "Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
- Effective amounts suitable for use in the method of invention may vary depending upon the particular formula I compound, target pest, method of application, application timing, weather conditions, animal pest habitat, especially insect, arachnid or acarid habitat, or the like. In general, for use in treating crop plants, the rate of application of the compounds I and/or compositions according to this invention may be in the range of about 0.1 g to about 4000 g per hectare, desirably from about 25 g to about 600 g per hectare, more desirably from about 50 g to about 500 g per hectare. For use in treating seeds, the typical rate of application is of from about 1 g to about 500 g per kilogram of seeds, desirably from about 2 g to about 300 g per kilogram of seeds, more desirably from about 10 g to about 200 g per kilogram of seeds. Customary application rates in the protection of materials are, for example, from about 0.001 g to about 2000 g, desirably from about 0.005 g to about 1000 g, of active compound per cubic meter of treated material.
- The compounds I or the pesticidal compositions comprising them can be used, for example in the form of solutions, emulsions, microemulsions, suspensions, flowable concentrates, dusts, powders, pastes and granules. The use form depends on the particular purpose; in any case, it should guarantee a fine and uniform distribution of the compound according to the invention.
- The pesticidal composition for combating animal pests, especially insects, acaridae and/or arachnids contains such an amount of at least one compound of the general formula I or an agriculturally useful salt of I and auxiliaries which are usually used in formulating pesticidal composition.
- The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly-disperse silica, silicates); emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
- Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.
- Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
- Powders, materials for scattering and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
- Granules, e.g. coated granules, compacted granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
- Such formulations or compositions of the present invention include a formula I compound of this invention (or combinations thereof) admixed with one or more agronomically acceptable inert, solid or liquid carriers. Those compositions contain a pesticidally effective amount of said compound or compounds, which amount may vary depending upon the particular compound, target pest, and method of use.
- In general, the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- The following are exemplary formulations:
I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient. II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a formulation of the active ingredient with good adhesion properties (comprises 23% by weight of active ingredient). III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient). IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient). V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient). VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (comprises 90% by weight of active ingredient). VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient. VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient. - The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, scattering or pouring. The use forms depend entirely on the intended purposes; in any case, this is intended to guarantee the finest possible distribution of the active ingredients according to the invention.
- Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
- The active ingredient concentrations in the ready-to-use products can be varied within substantial ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.
- The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even the active ingredient without additives.
- Compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
- These agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
- The following list of pesticides together with which the compounds of formula I can be used, is intended to illustrate the possible combinations, but not to impose any limitation:
- Organophosphates: Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fenthion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevinphos, Monocrotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprophos, Triazophos, Trichlorfon;
- Carbamates: Alanycarb, Benfuracarb, Carbaryl, Carbosulfan, Fenoxycarb, Furathiocarb, Indoxacarb, Methiocarb, Methomyl, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Triazamate;
- Pyrethroids: Bifenthrin, Cyfluthrin, Cypermethrin, Deltamethrin, Esfenvalerate, Ethofenprox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda-Cyhalothrin, Permethrin, Silafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta-Cypermethrin;
- Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron; Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Clofentazine; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: Spirodiclofen;
- Various: Abamectin, Acequinocyl, Amitraz, Azadirachtin, Bifenazate, Cartap, Chlorfenapyr, Chlordimeform, Cyromazine, Diafenthiuron, Dinetofuran, Diofenolan, Emamectin, Endosulfan, Ethiprole, Fenazaquin, Fipronil, Formetanate, Formetanate hydrochloride, Hydramethylnon, Imidacloprid, Indoxacarb, Pyridaben, Pymetrozine, Spinosad, Sulfur, Tebufenpyrad, Thiamethoxam, and Thiocyclam.
- The present invention is now illustrated in further detail by the following examples.
-
- 0.280 g (2.76 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.393 g (2.53 mmol) of cis-4-tert-butylcyclohexylamine were added successively to a solution of 0.500 g (2.3 mmol) of 5-ethyl-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.420 g (1.2 mmol, 52% of theory) of the title compound having a melting point of 120-122°C.
1H-NMR (CDCl3) δ: 8.25 (s, 1 H), 6.20 (m, 1 H), 5.20 (m, 1 H), 3.00 (q, 2H), 2.05 (d, 2H), 1.85 (s, 1 H), 1.70 (t, 4H), 1.35 (t, 3H), 1.30-1.10 (m, 2H), 0.90 (s, 9H). -
- 0.220 g (2.2 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.340 g (2.2 mmol) of cis-4-tert-butylcyclohexylamine were added successively to a solution of 0.470 g (2.0 mmol) of 5-(1-fluoroethyl)-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine in 15 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.540 g (1.5 mmol, 76% of theory) of the title compound having a melting point of 138-139°C.
1H-NMR (CDCl3) δ: 8.35 (s, 1 H), 6.35 (bd, 1 H), 6.00 (dq, 1 H), 5.25 (bm, 1 H), 2.00 (bd, 2H), 1.75 (dd, 3H), 1.70 (m, 3H), 1.30-1.10 (m, 4H), 0.90 (s, 9H). -
- 0.510 g (5.1 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 1.04 g (5.1 mmol) of 2-(4-trifluoromethoxyphenyl)-ethylamine were added successively to a solution of 1.0 g (4.6 mmol) of 5-ethyl-6,7-dichloro-[1,2,4]triazolo-[1,5-a]pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 1.60 g (5.0 mmol, 99% of theory) of the title compound having a melting point of 186-187 °C.
1H-NMR (CDCl3) δ: 8.25 (s, 1 H), 7.25 (d, 2H), 7.20 (d, 2H), 6.00 (bm, 1 H), 4.45 (q, 2H), 3.10 (t, 2H), 3.00 (q, 2H), 1.35 (t, 3H). -
- 0.300 g (3.0 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.514 g (3.7 mmol) of (S)-1-(4-fluorophenyl)-ethylamine were added successively to a solution of 0.500 g (2.5 mmol) of 5-methyl-6,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and with water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.520 g (1,7 mmol, 68% of theory) of the title compound having a melting point of 103-104°C.
1H-NMR (CDCl3) δ: 8.25 (s, 1 H), 7.30 (dd, 2H), 7.00 (t, 2H), 6.25 (m,1 H), 6.05 (bd, 1 H), 2.60 (s, 3H), 1.75 (d, 3H).; - The compounds of Inventive Examples 1 to 197 were listed in the following Table 1. The synthesis of compounds according to the invention not described was in an analogous manner as described above:
Table 1: Example No. R1 R2 R4 +) m.p. [°C] 1. H C2H5 cis-4-tert-butylcyclohexyl- 120-122 2. H CH3CHF cis-4-tert-butylcyclohexyl- 138-139 3. H CH3 4-methylcyclohexyl- 134-136 4. H CH3 4-tert-butylcyclohexyl- 165-167 5. H CH3 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 188-190 6. H CH3 4-((CH3)2CH)-cyclohexyl- 109-112 7. H CH3 4-tert-butylcyclohexyl- 130-134 8. H CH3 cis-4-sec.-butylcyclohexyl- 88-90 9. H CH3 trans-4-sec.-butylcyclohexyl- 149-150 10. H CH3 trans-4-tert-butylcyclohexyl- 138-140 11. H CH3 cis-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 162-165 12. H CH3 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 164-166 13. H C2H5 4-tert-butylcyclohexyl- 118-142 14. H C2H5 cis-4-sec.-butylcyclohexyl- 91-93 15. H C2H5 trans-4-tert-butylcyclohexyl- 183-184 16. H C2H5 trans-4-sec.-butylcyclohexyl- 164-165 17. H C2H5 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 177-179 18. H C2H5 4-methylcyclohexyl- 150-152 19. H C2H5 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 205-209 20. H C2H5 4-((CH3)2CH)-cyclohexyl- 140-144 21. H3CSO2 C2H5 cis-4-tert-butylcyclohexyl- resinous 22. H3CSO C2H5 cis-4-tert-butylcyclohexyl- 89-97 23. SCH3 C2H5 cis-4-tert-butylcyclohexyl- 125-128 24. H CF3 4-tert-butylcyclohexyl- 155-157 25. H CF3 4-methylcyclohexyl- 171-173 26. H CF3 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 191-193 27. H CF3 4-((CH3)2CH)-cyclohexyl- 160-161 28. H CH3CHCl cis-4-tert-butylcyclohexyl- 153-155 29. H CH3 (R)-indan-1-yl 108-111 30. H CH3 (S)-indan-1-yl 115-119 31. H C2H5 (R)-indan-1-yl 95-97 32. H C2H5 (S)-indan-1-yl 96-98 33. H CH3 (R)-1,2,3,4-tetrahydronaphthalen-1-yl 110-113 34. H CH3 (S)-1,2,3,4-tetrahydronaphthalen-1-yl 121-124 35. H C2H5 (R)-1,2,3,4-tetrahydronaphthalen-1-yl 80-81 36. H C2H5 (S)-1,2,3,4-tetrahydronaphthalen-1-yl 82-84 37. H CH3 4-F-C6H4- resinous 38. H CH3 C6H5- 200-201 39. H CH3 4-Cl-C6H4 138-141 40. H CH3 4-(C6H5)-C6H4- 139-141 41. H CH3 4-phenoxyphenyl 171-172 42. H CH3 4-((CH3)3C)-C6H4- 160-163 43. H C2H5 4-((CH3)3C)-C6H4- 182-185 44. H C2H5 phenyl 201-202 45. H C2H5 4-F-C6H4- 213-214 46. H C2H5 4-Cl-C6H4- 200-201 47. H C2H5 4-(C6H5)-C6H4- 159-162 48. H C2H5 4-phenoxyphenyl 183-185 49. H CF3 4-(C6H5)-C6H4- 209-210 50. H CF3 C6H5- 211-213 51. H CF3 4-F-C6H4- 193-196 52. H CF3 4-Cl-C6H4- 177-179 53. H CF3 4-phenoxyphenyl 190-193 54. H CH3CHF 4-tert-butylphenyl 183-186 55. H CH3 benzyl 129-130 56. H CH3 4-trifluoromethylbenzyl 128-132 57. H CH3 4-tert-butylbenzyl 164-168 58. H CH3 4-tert-butoxybenzyl 102-105 59. H CH3 3,4-Cl2C6H3-CH2- 195-200 60. H CH3 4-chlorobenzyl 171-175 61. H CH3 4-(4-methoxyphenoxy)phenyl-CH2- 132-136 62. H CH3 4-(4-tert-butylphenoxy)phenyl-CH2- resinous 63. H CH3 4-(4-bromophenoxy)phenyl-CH2- 150-152 64. H CH3 4-(4-ethylphenoxy)phenyl-CH2- 160-162 65. H CH3 4-(4-methylphenoxy)phenyl-CH2 156-158 66. H CH3 4-(4-chlorophenoxy)phenyl-CH2- 146-148 67. H CH3 4-(2-ethylphenoxy)phenyl-CH2- 157-159 68. H CH3 4-(3-ethylphenoxy)phenyl-CH2- resinous 69. H CH3 4-(2-bromophenoxy)phenyl-CH2- 162-164 70. H CH3 4-(3-chlorophenoxy)phenyl-CH2- 167-168 71. H CH3 4-(2-methylphenoxy)phenyl-CH2- 155-161 72. H CH3 4-(2-tert-butylphenoxy)phenyl-CH2- 152-155 73. H CH3 4-(2-chlorophenoxy)phenyl-CH2- 165-167 74. H CH3 4-(3-fluorophenoxy)phenyl-CH2- 167-174 75. H CH3 4-(3-bromophenoxy)phenyl-CH2 158-160 76. H CH3 4-(4-isopropylphenoxy)phenyl-CH2- 160-163 77. H CH3 4-(3-fluoro-4-chlorophenoxy)phenyl-CH2- 106-108 78. H CH3 4-(3-chloro-4-bromophenoxy)phenyl-CH2- 135-138 79. H CH3 4-(3-chloro-4-methylphenoxy)phenyl-CH2- 138-140 80. H CH3 4-(3,4-difluorophenoxy)phenyl-CH2- 121-124 81. H CH3 4-(3-methyl-4-chlorophenoxy)phenyl-CH2- 145-148 82. H CH3 4-(3,4-dimethylphenoxy)phenyl-CH2- 157-159 83. H CH3 4-(3-chloro-4-fluorophenoxy)phenyl-CH2- 122-125 84. H CH3 4-(3,4-dichlorophenoxy)phenyl-CH2- resinous 85. H CH3 4-(3-methyl-4-bromophenoxy)phenyl-CH2- 158-160 86. H C2H5 4-(4-ethylphenoxy)phenyl-CH2- resinous 87. H C2H5 benzyl 115-116 88. H C2H5 3,4-Cl2C6H3-CH2- 181-184 89. H C2H5 4-F3C-C6H4-CH2- 169-171 90. H C2H5 4-tert-butylphenyl-CH2- 111-113 91. H C2H5 4-(4-tert-butoxy)-C6H4-CH2- 80-85 92. H C2H5 4-Cl-C6H4-CH2- 142-146 93. H C2H5 4-(4-methoxyphenoxy)phenyl-CH2- 100-106 94. H CF3 C6H5-CH2- 154-156 95. H CF3 4-tert-butylphenyl-CH2- 109-111 96. H CH3 C6H5-CH2CH2- 161-163 97. H CH3 4-Cl-C6H4-CH2CH2- 165-167 98. H CH3 4-F-C6H4-CH2CH2- 180-182 99. H CH3 4-F3C-C6H4-CH2CH2- 185-187 100. H CH3 3,4-(CH3O)2C6H3-CH2CH2- 161-163 101. H CH3 4-tert-butylphenyl-CH2CH2- 150-151 102. H CH3 4-F3C-O-C6H4CH2CH2- 182-184 103. H C2H5 4-F-C6H4-CH2CH2- 162-165 104. H C2H5 4-F3C-C6H4-CH2CH2- 179-183 105. H C2H5 4-trifluoromethoxy-C6H4CH2CH2- 186-187 106. H C2H5 C6H5-CH2CH2- 158-160 107. H C2H5 4-Cl-C6H4-CH2CH2- 170-172 108. H C2H5 3,4-(CH3O)2C6H3-CH2CH2- 143-145 109. H C2H5 4-tert-butylphenyl-CH2CH2- 172-174 110. H CF3 4-tert-butylphenyl-CH2CH2- 176-178 111. H CF3 C6H5-CH2CH2- 161-163 112. H CF3 3,4-(CH3O)2C6H3-CH2CH2- 183-186 113. H CH3CHF 4-trifluoromethoxy-C6H4-CH2CH2- 167-168 114. H CH3 (S)-4-F-C6H4-CH(CH3)- 103-104 115. H CH3 4-Cl-C6H4-CH(CH3)- 93-95 116. H CH3 4-F-C6H4-CH(CH3)- 75-77 117. H CH3 (R)-C6H5-CH(CH3)- 95-98 118. H C2H5 4-Cl-C6H4-CH(CH3)- resinous 119. H CH3 4-Br-C6H4-CH(CH3)- 79-82 120. H CH3 (S)-4-Cl-C6H4-CH(CH3)- 122-123 121. H CH3 (S)-4-CH3O-C6H4-CH(CH3)- 107-108 122. H CH3 (S)-4-CH3-C6H4-CH(CH3)- 164-166 123. H CH3 3,4-Cl2C6H3-CH(CH3)- 103-105 124. H CH3 3-ClC6H4-CH(CH3)- 105-108 125. H CH3 4-F3C-C6H4-CH(CH3)- 85-88 126. H CH3 (S)-C6H5-CH(CH3)- resinous 127. H CH3 4-(4-CH3-C6H4-O)-C6H4-CH(CH3)- 136-140 128. H CH3 (R)-4-CH3-C6H4-CH(CH3)- 156-159 129. H CH3 (R)-4-Cl-C6H4-CH(CH3)- 117-122 130. H CH3 (R)-4-Br-C6H4-CH(CH3)- 116-119 131. H CH3 (S)-4-Br-C6H4-CH(CH3)- 114-130 132. H CH3 (R)-4-F-C6H4-CH(CH3)- 105-107 133. H CH3 (R)-3-CH3O-C6H4-CH(CH3)- 86-110 134. H CH3 (S)-3-CH3O-C6H4-CH(CH3)- 83-100 135. H CH3 4-CF3O-C6H4-CH(CH3)- 98-101 136. H CH3 (R)-4-CH3O-C6H4-CH(CH3)- 99-136 137. H CH3 (R)-3-(C6H5-CH2-O)-C6H4-CH(CH3)- resinous 138. H CH3 (S)-4-benzyloxy-C6H4-CH(CH3)- resinous 139. H CH3 (R)-(naphthalen-1-yl)-CH(CH3)- 118-120 140. H CH3 (S)-(naphthalen-1-yl)-CH(CH3)- 117-120 141. H CH3 (R)-(naphthalen-2-yl)-CH(CH3)- 100-103 142. H CH3 (S)-(naphthalen-2-yl)-CH(CH3)- 89-91 143. H CH3 4-(C6H5)-C6H4-CH(CH3)- 81-88 144. H CH3 1,1,2,3,3-pentamethylindan-5-yl-CH(CH3)- resinous 145. H CH3 (R)-cyclohexyl-CH(CH3)- resinous 146. H CH3 (S)-cyclohexyl-CH(CH3)- resinous 147. H C2H5 (R)-cyclohexyl-CH(CH3)- resinous 148. H C2H5 (S)-cyclohexyl-CH(CH3)- resinous 149. H C2H5 4-Br-C6H4-CH(CH3)- resinous 150. H C2H5 4-F-C6H4-CH(CH3)- 97-98 151. H C2H5 (R)-C6H5CH(CH3)- 77-80 152. H C2H5 (S)-C6H5CH(CH3)- resinous 153. H C2H5 3,4-Cl2C6H3-CH(CH3)- 148-150 154. H C2H5 3-ClC6H4-CH(CH3)- resinous 155. H C2H5 4-F3C-C6H4-CH(CH3)- resinous 156. H C2H5 (S)-4-CH3O-C6H4-CH(CH3)- resinous 157. H C2H5 (S)-4-CH3-C6H4-CH(CH3)- 55-58 158. H C2H5 (R)-4-CH3-C6H4-CH(CH3)- 63-67 159. H C2H5 (S)-4-Br-C6H4-CH(CH3)- resinous 160. H C2H5 (R)-4-Br-C6H4-CH(CH3)- resinous 161. H C2H5 (S)-4-F-C6H4-CH(CH3)- resinous 162. H C2H5 (R)-4-F-C6H4-CH(CH3)- resinous 163. H C2H5 (S)-4-Cl-C6H4-CH(CH3)- resinous 164. H C2H5 (R)-4-Cl-C6H4-CH(CH3)- resinous 165. H C2H5 (R)-4-NO2-C6H4-CH(CH3)- 98-105 166. H C2H5 (S)-4-NO2-C6H4-CH(CH3)- 98-105 167. H C2H5 (R)-3-CH3O-C6H4-CH(CH3)- resinous 168. H C2H5 (S)-3-CH3O-C6H4-CH(CH3)- resinous 169. H C2H5 (R)-4-CH3O-C6H4-CH(CH3)- resinous 170. H C2H5 4-F3C-O-C6H4-CH(CH3)- 122-124 171. H C2H5 4-tert-butyl-C6H4-CH(CH3)- 93-96 172. H C2H5 (R)-4-(benzyloxy)-C6H4-CH(CH3)- resinous 173. H C2H5 (S)-4-(benzyloxy)-C6H4-CH(CH3)- resinous 174. H C2H5 (R)-(naphthalen-1-yl)-CH(CH3)- 107-111 175. H C2H5 (S)-(naphthalen-1-yl)-CH(CH3)- 111-112 176. H C2H5 (R)-(naphthalen-2-yl)-CH(CH3)- 117-119 177. H C2H5 (S)-(naphthalen-2-yl)-CH(CH3)- 115-117 178. H C2H5 4-C6H5-C6H4-CH(CH3)- 53-70 179. H C2H5 1,1,2,3,3-pentamethylindan-5-yl-CH(CH3)- resinous 180. H3CS C2H5 (S)-4-Cl-C6H4-CH(CH3)- 128-131 181. H CH3CHF (R)-4-CH3-C6H4-CH(CH3)- resinous 182. H CH3CHF (R)-4-F-C6H4-CH(CH3)- resinous 183. H CH3CHF (R)-4-Cl-C6H4-CH(CH3)- resinous 184. H CH3CHF 4-F3C-O-C6H4-CH(CH3)- 142-151 185. H CH3CHF 4-tert-butyl-C6H4-CH(CH3)- 102-115 186. H CH3CHF (S)-4-F-C6H4-CH(CH3)- resinous 187. H CH3CHF (S)-4-Cl-C6H4-CH(CH3)- resinous 188. H CH3CHF (S)-4-Br-C6H4-CH(CH3)- resinous 189. H CH3 (2,2-difluorobenzodioxole-5-yl)C(C2H5)H- resinous 190. H CH3 (R)-C6H5CH(CH2CH3)- 65-120 191. H CH3 (S)-C6H5CH(CH2CH3)- 63-92 192. H C2H5 (R)-C6H5CH(CH2CH3)- resinous 193. H C2H5 (S)-C6H5CH(CH2CH3)- resinous 194. H CH3 (R)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 48-53 195. H CH3 (S)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 65-66 196. H C2H5 (R)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 70-72 197. H C2H5 (S)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 67-69 198. H CH3 (S)-2-H3C-O-C6H4-CH(CH3)- Oil 199. H C2H5 (S)-2-H3C-O-C6H4-CH(CH3)- 64-69 200. H CH3 4-cyclo-C6H11-C6H4-CH(CH3)- Oil 201. H C2H5 4-cyclo-C6H11-C6H4-CH(CH3)- 110-113 202. H CH3 4-(H3C)2CH-C6H4-CH(CH3)- Oil 203. H C2H5 4-(H3C)2CH-C6H4-CH(CH3)- 75-77 204. H CH3 110-112 205. H C2H5 Oil 206. H CH3 62-67 207. H C2H5 59-64 208. H CH3 83-88 209. H C2H5 Oil 210. H CH3 (S)-2,4-Cl2-C6H3-CH(CH3)- 92-94 211. H C2H5 S)-2,4-Cl2-C6H3-CH(CH3)- 45-47 212. SOCH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- 96-108 213. SO2CH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- Oil 214. SCH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- 60-66 215. SCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- 88-96 216. SCH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- 138-141 217. SCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 69-72 218. SOCH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- Oil 219. SO2CH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- Oil 220. SOCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- Oil 221. SO2CH3 C2H5 (S)-4-F-C6H4-CH(CH3)- Oil 222. SO2CH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- 65-105 223. SCH3 C2H5 4-tert.-butyl-C6H4- 191-193 224. SCH3 C2H5 4-F3CO-C6H4-CH2-CH2- 103-105 225. OCH3 C2H5 cis-4-tert.-butyl-cyclo-C6H11- 123-131 226. SO2CH3 C2H5 4-tert.-butyl-C6H4- 205-211 227. SOCH3 C2H5 4-tert.-butyl-C6H4- 240-243 228. SOCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 229. SO2CH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 230. SO2CH3 C2H5 4-F3CO-C6H4-CH2-CH2- 162-167 231. SOCH3 C2H5 4-F3CO-C6H4-CH2-CH2- 146-149 232. H C2H5 4-tert.-butyl-C6H4-CH(CH3)- Oil 233. H CH3 (R)-2-H3C-O-C6H4-CH(CH3)- Oil 234. H C2H5 (R)-2-H3C-O-C6H4-CH(CH3)- 63-68 235. H CH3 (R)-2,4-Cl2-C6H3-CH(CH3)- 84-90 236. H C2H5 (R)-2,4-Cl2-C6H3-CH(CH3)- 46-51 237. H C2H5 2-F-C6H4-CH(CH3)- 92-95 238. H CH3 2-Cl-6-F-C6H3-CH(CH3)- 106-109 239. H C2H5 2-Cl-6-F-C6H3-CH(CH3)- 91-95 240. H CH3 2-F-C6H4-CH(CH3)- 104-105 241. H CH3 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- 100-103 242. H C2H5 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- Oil 243. H CH3 (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- 100-102 244. H C2H5 (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- Oil 245. H CH3 2,4-F2-C6H3-CH(CH3)- 139-140 246. H C2H5 2,4-F2-C6H3-CH(CH3)- 113-115 247. H CH3 4-Cl-2-F-C6H3-CH(CH3)- 106-109 248. H C2H5 4-Cl-2-F-C6H3-CH(CH3)- 97-99 249. OCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- Oil 250. OCH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- Oil 251. OCH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- Oil 252. a C2H5 cis-4-tert.-butyl-cyclo-C6H11- 102-105 253. b C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 254. c C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 255. d C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 256. e C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 257. f C2H5 cis-4-tert.-butyl-cyclo-C6H11- 110-143 258. g C2H5 cis-4-tert.-butyl-cyclo-C6H11- 75-90 259. h C2H5 cis-4-tert.-butyl-cyclo-C6H11- 78-85 260. i C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 261. CN C2H5 cis-4-tert.-butyl-cyclo-C6H11- 151-153 262. OCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 58-69 263. OH C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 264. k C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 265. H CH3 4-F2HCO-C6H4-CH(CH3)- 90-91 266. H C2H5 4-F2HCO-C6H4-CH(CH3)- 102-103 267. H CH3 4-F2HC-CF2O-C6H4-CH(CH3)- 85-86 268. H C2H5 4-F2HC-CF2O-C6H4-CH(CH3)- 82-83 m.p. = melting point
+ (S) refers always to the configuration of CH(CH3) at the nitrogen atom; and * indicates the position at which the radical is bound to the remainder of the molecule
a: H3CO-C(O)-CH2-S-; b: H3CO-CH2CH2-S- ; c: H3CO-C(O)-CH2CH2-S-;
d: H3CO-CH2CH2-O-; e: H3CO-CH2CH2-O-CH2CH2-O-; f: HO-C(O)-CH2-S-;
g: H3C-CH2-O-; h: (H3C)2CH-O-; i: HC≡C-CH2-O-; k: H5C6-CH2-O- - The action of the compounds of the formula I against pests was demonstrated by the following experiments:
- The active compounds were formulated
- a. for testing the activity against Aphis gossypii, Tetranychus urticae, Myzus persicae, and Aphis fabae, as 50:50 acetone:water solutions amended with 100 ppm Kinetic ® (surfactant),
- b. for testing the activity against Spodoptera eridania as a 10.000 ppm solution in a mixture of 35% acetone and water, which was diluted with water, if needed,
- c. for testing the activity against Nilaparvata lugens and Sogatella furcifera as a 20:80 acetone:water solution. Surfactant (Alkamuls EL 620) was added at the rate of 0.1% (vol/vol).
- After the experiments were completed, in each case the lowest concentration was determined at which the compound still caused an 75 to 100% inhibition or mortality in comparison with untreated controls (limit or minimal concentration).
- Cotton plants in the cotyledon stage (variety 'Delta Pine') are infested with approximately 100 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The cotyledons of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.
- In this test, compounds of examples nos 1, 4, 5, 6, 7, 8, 13, 14, 18, 19, 20, 58, 62, 65, 66, 68, 76, 80, 91, 101, 108, 114, 115, 116, 118, 119, 120, 121, 122, 126, 150, 152, 156, 157, 158, 159, 160, 161, 162, 163 and 189 at 300 ppm showed over 75% mortality in comparison with untreated controls.
- Lima bean plants in the 1st leaf-pair stage (variety 'Henderson') are infested with approximately 100 laboratory-reared mites per leaf by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The foliage of the intact plants is dipped into gradient solutions of the test compound. Mite mortality is determined after 5 days.
- In this test, compounds of examples nos. 1, 5, 52 56, 57, 58, 59, 60, 78, 82, 84, 87, 90, 91, 101, 115, 119 and 120 at 300 ppm showed over 75% mortality in comparison with untreated controls.
- Pepper plants in the 2nd leaf-pair stage (variety 'California Wonder') are infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The leaves of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.
- In this test, compounds of examples nos. 1, 4, 5, 6, 7, 8, 13, 14, 19, 20, 55, 57, 89, 106, 107, 109, 114, 115, 116, 118, 119, 120, 121, 122, 123, 125, 126, 152, 156, 157, 158, 159, 160, 161, 162, 163 and 189 at 300 ppm showed a 100% mortality in comparison with untreated controls.
- Nasturtium plants in the 1st leaf-pair stage (variety 'Mixed Jewel') are infested with approximately 25 laboratory-reared aphids by placing infested cut plants on top of the test plants. The cut plants are removed after 24 hr. The foliage and stem of the test plants are dipped into gradient solutions of the test compound. Aphid mortality is determined after 3 days.
- In this test, compounds of examples nos. 1, 5, 6, 76, 120, 126, 149, 161 and 163 at 300 ppm showed over 75% mortality in comparison with untreated controls.
- Foliage of two Sieva lima beans plants at the first expanded true-leaf stage that are contained within a single 3.8 cm square plastic pot are dipped into the test solution with agitation for 3 seconds and allowed to dry in a hood. The pot is then placed in a 25.4 cm plastic zipper top bag and infested with ten 2nd instar caterpillars. At 5 days, observations are made of mortality, reduced feeding, or any interference with normal molting.
- In this test, compounds of examples nos. 51, 80, 119, 159, 161 and 163 at 300 ppm showed over 75% mortality in comparison with untreated controls.
Brown Plant Hopper (Nilaparvata lugens)
White-backed Plant Hopper (Sogatella furcifera) - Potted rice plants of 3-4 weeks of age are sprayed with 10 ml of the test solution using air driven hand atomizer (Devillbis atomizer) at 1.7 bar. The treated plants are allowed to dry for about 1 hour and covered with Mylar cages. The plants are inoculated with 10 adults of each species (5 male and 5 females) and kept at 25-27oC and 50-60% humidity for 3 days. Mortality is assed after 24, 48 and 72 hours after treatment. Dead insects are usually found in the water surface. Each treatment is replicated once.
- In this test, compounds I at 500 ppm showed over 75% mortality of Nilaparvata lugens in comparison with untreated controls.
- In this test, compounds I at 500 ppm showed over 75% mortality of Sogatella furcifera in comparison with untreated controls.
Claims (18)
- A non-therapeutic method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula IX is halogen;R1 is hydrogen, halogen, OH, CN, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C2-C10-alkenyl, phenyl, phenoxy, benzyloxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy or C2-C10-alkynyl, wherein C1-C10-alkylthio, C1-C10-alkylsulfinyl and C1-C10-alkylsulfonyl may be unsubstituted or partially or completely substituted with halogen and/or may carry a group selected from C1-C4-alkoxy, C1-C4-alkoxycarbonyl or COOH;R2 is C1-C10-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C10-cycloalkyl, C2-C10-alkenyl or C2-C10-alkynyl;R3 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl or arylcarbonyl;R4 is C3-C10-cycloalkyl, phenyl, naphthyl, 3- to 7-membered heterocyclyl or a radical of the formula -A-R4a, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3- to 7-membered heterocyclyl to be unsubstituted or to carry 1, 2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkyl, C1-C10-haloalkoxy, amino, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen,and/or at least one agriculturally acceptable salt thereof.
and wherein heterocyclyl contains 1, 2 or 3 heteroatoms selected, independently from each other, from the group consisting of oxygen, sulfur, nitrogen and a group NR5,
it being also possible for C3-C10-cycloalkyl, phenyl and 3- to 7-membered heterocyclyl to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl; whereinA is a C1-C6-alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfur;R4a is C3-C10-cycloalkyl, phenyl, naphthyl or 3- to 7-membered heterocyclyl, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3- to 7-membered heterocyclyl to be unsubstituted or to carry 1, 2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkyl, C1-C10-haloalkoxy, amino, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen,
and wherein heterocyclyl contains 1, 2 or 3 heteroatoms selected, independently from each other, from the group consisting of oxygen, sulfur, nitrogen and a group NR5,
it being also possible for C3-C10-cycloalkyl, phenyl and 3- to 7-membered heterocyclyl to be fused to a 5- to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5- to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may it-self carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl; andR5 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; - The method as claimed in claim 1, wherein the radical R1 in formula I is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl.
- The method as claimed in claim 2, wherein the radical R1 in formula I is hydrogen.
- The method as claimed in claim 1, wherein the radical R2 in formula I is C1-C4-alkyl or C1-C4-haloalkyl.
- The method as claimed in claim 4, wherein the radical R2 in formula I is C1-C2-alkyl or C1-C2-fluoroalkyl.
- The method as claimed in claim 1, wherein the radical R3 in formula I is hydrogen or C1-C4-alkoxy-C1-C4-alkyl.
- The method as claimed in claim 6, wherein the radical R3 in formula I is hyd rogen.
- The method as claimed in claim 1, wherein the radical R4 in formula I is phenyl, phenyl-C1-C4-alkyl or C3-C8-cycloalkyl, wherein each phenyl and C3-C8-cycloalkyl group may be unsubstituted or may carry one or two substituents as defined above.
- The method as claimed in claim 8, wherein the radical R4 in formula I is cyclohexyl which carries a substituent in the 4-position.
- The method as claimed in claim 9, wherein the substituent is C1-C4-alkyl.
- The method as claimed in claim 8, wherein the radical R4 in formula I is 1-phenylethyl which carries a substituent in the 4-position.
- The method as claimed in claim 11, wherein the substituent is selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl and C1-C4-haloalkoxy.
- The method as claimed in claim 1, wherein the radical X in formula I is chlorine.
- A method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of a 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I and/or at least one salt thereof as defined in claim 1.
- The non-therapeutic use of 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I as defined in claim 1 and of their agriculturally acceptable salts for combating animal pests.
- The use of 6-halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidine of the general formula I as defined in claim 1 and of their agriculturally acceptable salts for protecting crops from attack or infestation by animal pests.
- 6-Halogeno-[1,2,4]-triazolo[1,5-a]-pyrimidines of formula I
Example No. R1 R2 R4 +) 1. H C2H5 cis-4-tert-butylcyclohexyl- 2. H CH3CHF cis-4-tert-butylcyclohexyl- 3. H CH3 4-methylcyclohexyl- 4. H CH3 4-tert-butylcyclohexyl- 5. H CH3 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 6. H CH3 4-((CH3)2CH)-cyclohexyl- 7. H CH3 4-tert-butylcyclohexyl- 8. H CH3 cis-4-sec.-butylcyclohexyl- 9. H CH3 trans-4-sec.-butylcyclohexyl- 10. H CH3 trans-4-tert-butylcyclohexyl- 11. H CH3 cis-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 12. H CH3 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 13. H C2H5 4-tert-butylcyclohexyl- 14. H C2H5 cis-4-sec.-butylcyclohexyl- 15. H C2H5 trans-4-tert-butylcyclohexyl- 16. H C2H5 trans-4-sec.-butylcyclohexyl- 17. H C2H5 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 18. H C2H5 4-methylcyclohexyl- 19. H C2H5 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 20. H C2H5 4-((CH3)2CH)-cyclohexyl- 21. H3CSO2 C2H5 cis-4-tert-butylcyclohexyl- 22. H3CSO C2H5 cis-4-tert-butylcyclohexyl- 23. SCH3 C2H5 cis-4-tert-butylcyclohexyl- 24. H CF3 4-tert-butylcyclohexyl- 25. H CF3 4-methylcyclohexyl- 26. H CF3 4-(cyclohexyl-C(CH3)2)-cyclohexyl- 27. H CF3 4-((CH3)2CH)-cyclohexyl- 28. H CH3CHCl cis-4-tert-butylcyclohexyl- 29. H CH3 (R)-indan-1-yl 30. H CH3 (S)-indan-1-yl 31. H C2H5 (R)-indan-1-yl 32. H C2H5 (S)-indan-1-yl 33. H CH3 (R)-1,2,3,4-tetrahydronaphthalen-1-yl 34. H CH3 (S)-1,2,3,4-tetrahydronaphthalen-1-yl 35. H C2H5 (R)-1,2,3,4-tetrahydronaphthalen-1-yl 36. H C2H5 (S)-1,2,3,4-tetrahydronaphthalen-1-yl 37. H CH3 4-F-C6H4- 38. H CH3 C6H5- 39. H CH3 4-Cl-C6H4 40. H CH3 4-(C6H5)-C6H4- 41. H CH3 4-phenoxyphenyl 42. H CH3 4-((CH3)3C)-C6H4- 43. H C2H5 4-((CH3)3C)-C6H4- 44. H C2H5 phenyl 45. H C2H5 4-F-C6H4- 46. H C2H5 4-Cl-C6H4- 47. H C2H5 4-(C6H5)-C6H4- 48. H C2H5 4-phenoxyphenyl 49. H CF3 4-(C6H5)-C6H4- 50. H CF3 C6H5- 51. H CF3 4-F-C6H4- 52. H CF3 4-Cl-C6H4- 53. H CF3 4-phenoxyphenyl 54. H CH3CHF 4-tert-butylphenyl 55. H CH3 benzyl 56. H CH3 4-trifluoromethylbenzyl 57. H CH3 4-tert-butylbenzyl 58. H CH3 4-tert-butoxybenzvl 59. H CH3 3,4-Cl2C6H3-CH2- 60. H CH3 4-chlorobenzyl 61. H CH3 4-(4-methoxyphenoxy)phenyl-CH2- 62. H CH3 4-(4-tert-butylphenoxy)phenyl-CH2- 63. H CH3 4-(4-bromophenoxy)phenyl-CH2- 64. H CH3 4-(4-ethylphenoxy)phenyl-CH2- 65. H CH3 4-(4-methylphenoxy)phenyl-CH2 66. H CH3 4-(4-chlorophenoxy)phenyl-CH2- 67. H CH3 4-(2-ethylphenoxy)phenyl-CH2- 68. H CH3 4-(3-ethylphenoxy)phenyl-CH2- 69. H CH3 4-(2-bromophenoxy)phenyl-CH2- 70. H CH3 4-(3-chlorophenoxy)phenyl-CH2- 71. H CH3 4-(2-methylphenoxy)phenyl-CH2- 72. H CH3 4-(2-tert-butylphenoxy)phenyl-CH2- 73. H CH3 4-(2-chlorophenoxy)phenyl-CH2- 74. H CH3 4-(3-fluorophenoxy)phenyl-CH2- 75. H CH3 4-(3-bromophenoxy)phenyl-CH2 76. H CH3 4-(4-isopropylphenoxy)phenyl-CH2- 77. H CH3 4-(3-fluoro-4-chlorophenoxy)phenyl-CH2- 78. H CH3 4-(3-chloro-4-bromophenoxy)phenyl-CH2- 79. H CH3 4-(3-chloro-4-methylphenoxy)phenyl-CH2- 80. H CH3 4-(3,4-difluorophenoxy)phenyl-CH2- 81. H CH3 4-(3-methyl-4-chlorophenoxy)phenyl-CH2- 82. H CH3 4-(3,4-dimethylphenoxy)phenyl-CH2- 83. H CH3 4-(3-chloro-4-fluorophenoxy)phenyl-CH2- 84. H CH3 4-(3,4-dichlorophenoxy)phenyl-CH2- 85. H CH3 4-(3-methyl-4-bromophenoxy)phenyl-CH2- 86. H C2H5 4-(4-ethylphenoxy)phenyl-CH2- 87. H C2H5 benzyl 88. H C2H5 3,4-Cl2C6H3-CH2- 89. H C2H5 4-F3C-C6H4-CH2- 90. H C2H5 4-tert-butylphenyl-CH2- 91. H C2H5 4-(4-tert-butoxy)-C6H4-CH2- 92. H C2H5 4-Cl-C6H4-CH2- 93. H C2H5 4-(4-methoxyphenoxy)phenyl-CH2- 94. H CF3 C6H5-CH2- 95. H CF3 4-tert-butylphenyl-CH2- 96. H CH3 C6H5-CH2CH2- 97. H CH3 4-Cl-C6H4-CH2CH2- 98. H CH3 4-F-C6H4-CH2CH2- 99. H CH3 4-F3C-C6H4-CH2CH2- 100. H CH3 3,4-(CH3O)2C6H3-CH2CH2- 101. H CH3 4-tert-butylphenyl-CH2CH2- 102. H CH3 4-F3C-O-C6H4CH2CH2- 103. H C2H5 4-F-C6H4-CH2CH2- 104. H C2H5 4-F3C-C6H4-CH2CH2- 105. H C2H5 4-trifluoromethoxy-C6H4CH2CH2- 106. H C2H5 C6H5-CH2CH2- 107. H C2H5 4-Cl-C6H4-CH2CH2- 108. H C2H5 3,4-(CH3O)2C6H3-CH2CH2- 109. H C2H5 4-tert-butylphenyl-CH2CH2- 110. H CF3 4-tert-butylphenyl-CH2CH2- 111. H CF3 C6H5-CH2CH2- 112. H CF3 3,4-(CH3O)2C6H3-CH2CH2- 113. H CH3CHF 4-trifluoromethoxy-C6H4-CH2CH2- 114. H CH3 (S)-4-F-C6H4-CH(CH3)- 115. H CH3 4-Cl-C6H4-CH(CH3)- 116. H CH3 4-F-C6H4-CH(CH3)- 117. H CH3 (R)-C6H5-CH(CH3)- 118. H C2H5 4-Cl-C6H4-CH(CH3)- 119. H CH3 4-Br-C6H4-CH(CH3)- 120. H CH3 (S)-4-Cl-C6H4-CH(CH3)- 121. H CH3 (S)-4-CH3O-C6H4-CH(CH3)- 122. H CH3 (S)-4-CH3-C6H4-CH(CH3)- 123. H CH3 3,4-Cl2C6H3-CH(CH3)- 124. H CH3 3-ClC6H4-CH(CH3)- 125. H CH3 4-F3C-C6H4-CH(CH3)- 126. H CH3 (S)-C6H5-CH(CH3)- 127. H CH3 4-(4-CH3-C6H4-O)-C6H4-CH(CH3)- 128. H CH3 (R)-4-CH3-C6H4-CH(CH3)- 129. H CH3 (R)-4-Cl-C6H4-CH(CH3)- 130. H CH3 (R)-4-Br-C6H4-CH(CH3)- 131. H CH3 (S)-4-Br-C6H4-CH(CH3)- 132. H CH3 (R)-4-F-C6H4-CH(CH3)- 133. H CH3 (R)-3-CH3O-C6H4-CH(CH3)- 134. H CH3 (S)-3-CH3O-C6H4-CH(CH3)- 135. H CH3 4-CF3O-C6H4-CH(CH3)- 136. H CH3 (R)-4-CH3O-C6H4-CH(CH3)- 137. H CH3 (R)-3-(C6H5-CH2-O)-C6H4-CH(CH3)- 138. H CH3 (S)-4-benzyloxy-C6H4-CH(CH3)- 139. H CH3 (R)-(naphthalen-1-yl)-CH(CH3)- 140. H CH3 (S)-(naphthalen-1-yl)-CH(CH3)- 141. H CH3 (R)-(naphthalen-2-yl)-CH(CH3)- 142. H CH3 (S)-(naphthalen-2-yl)-CH(CH3)- 143. H CH3 4-(C6H5)-C6H4-CH(CH3)- 144. H CH3 1,1,2,3,3-pentamethylindan-5-yl-CH(CH3)- 145. H CH3 (R)-cyclohexyl-CH(CH3)- 146. H CH3 (S)-cyclohexyl-CH(CH3)- 147. H C2H5 (R)-cyclohexyl-CH(CH3)- 148. H C2H5 (S)-cyclohexyl-CH(CH3)- 149. H C2H5 4-Br-C6H4-CH(CH3)- 150. H C2H5 4-F-C6H4-CH(CH3)- 151. H C2H5 (R)-C6H5CH(CH3)- 152. H C2H5 (S)-C6H5CH(CH3)- 153. H C2H5 3,4-Cl2C6H3-CH(CH3)- 154. H C2H5 3-ClC6H4-CH(CH3)- 155. H C2H5 4-F3C-C6H4-CH(CH3)- 156. H C2H5 (S)-4-CH3O-C6H4-CH(CH3)- 157. H C2H5 (S)-4-CH3-C6H4-CH(CH3)- 158. H C2H5 (R)-4-CH3-C6H4-CH(CH3)- 159. H C2H5 (S)-4-Br-C6H4-CH(CH3)- 160. H C2H5 (R)-4-Br-C6H4-CH(CH3)- 161. H C2H5 (S)-4-F-C6H4-CH(CH3)- 162. H C2H5 (R)-4-F-C6H4-CH(CH3)- 163. H C2H5 (S)-4-Cl-C6H4-CH(CH3)- 164. H C2H5 (R)-4-Cl-C6H4-CH(CH3)- 165. H C2H5 (R)-4-NO2-C6H4-CH(CH3)- 166. H C2H5 (S)-4-NO2-C6H4-CH(CH3)- 167. H C2H5 (R)-3-CH3O-C6H4-CH(CH3)- 168. H C2H5 (S)-3-CH3O-C6H4-CH(CH3)- 169. H C2H5 (R)-4-CH3O-C6H4-CH(CH3)- 170. H C2H5 4-F3C-O-C6H4-CH(CH3)- 171. H C2H5 4-tert-butyl-C6H4-CH(CH3)- 172. H C2H5 (R)-4-(benzyloxy)-C6H4-CH(CH3)- 173. H C2H5 (S)-4-(benzyloxy)-C6H4-CH(CH3)- 174. H C2H5 (R)-(naphthalen-1-yl)-CH(CH3)- 175. H C2H5 (S)-(naphthalen-1-yl)-CH(CH3)- 176. H C2H5 (R)-(naphthalen-2-yl)-CH(CH3)- 177. H C2H5 (S)-(naphthalen-2-yl)-CH(CH3)- 178. H C2H5 4-C6H5-C6H4-CH(CH3)- 179. H C2H5 1,1,2,3,3-pentamethylindan-5-yl-CH(CH3)- 180. H3CS C2H5 (S)-4-Cl-C6H4-CH(CH3)- 181. H CH3CHF (R)-4-CH3-C6H4-CH(CH3)- 182. H CH3CHF (R)-4-F-C6H4-CH(CH3)- 183. H CH3CHF (R)-4-Cl-C6H4-CH(CH3)- 184. H CH3CHF 4-F3C-O-C6H4-CH(CH3)- 185. H CH3CHF 4-tert-butyl-C6H4-CH(CH3)- 186. H CH3CHF (S)-4-F-C6H4-CH(CH3)- 187. H CH3CHF (S)-4-Cl-C6H4-CH(CH3)- 188. H CH3CHF (S)-4-Br-C6H4-CH(CH3)- 189. H CH3 (2,2-difluorobenzodioxole-5-yl)C(C2H5)H- 190. H CH3 (R)-C6H5CH(CH2CH3)- 191. H CH3 (S)-C6H5CH(CH2CH3)- 192. H C2H5 (R)-C6H5CH(CH2CH3)- 193. H C2H5 (S)-C6H5CH(CH2CH3)- 194. H CH3 (R)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 195. H CH3 (S)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 196. H C2H5 (R)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 197. H C2H6 (S)-C6H5-CH2-O-CH2-CH2-CH(CH3)- 198. H CH3 (S)-2-H3C-O-C6H4-CH(CH3)- 199. H C2H5 (S)-2-H3C-O-C6H4-CH(CH3)- 200. H CH3 4-cyclo-C6H11-C6H4-CH(CH3)- 201. H C2H5 4-cyclo-C6H11-C6H4-CH(CH3)- 202. H CH3 4-(H3C)2CH-C6H4-CH(CH3)- 203. H C2H5 4-(H3C)2CH-C6H4-CH(CH3)- 204. H CH3 205. H C2H5 206. H CH3 207. H C2H5 208. H CH3 209. H C2H5 210. H CH3 (S)-2,4-Cl2-C6H3-CH(CH3)- 211. H C2H5 S)-2,4-Cl2-C6H3-CH(CH3)- 212. SOCH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- 213. SO2CH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- 214. SCH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- 215. SCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- 216. SCH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- 217. SCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 218. SOCH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- 219. SO2CH3 C2H5 (S)-4-CH3-C6H4-CH(CH3)- 220. SOCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- 221. SO2CH3 C2H5 (S)-4-F-C6H4-CH(CH3)- 222. SO2CH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- 223. SCH3 C2H5 4-tert.-butyl-C6H4- 224. SCH3 C2H5 4-F3CO-C6H4-CH2-CH2- 225. OCH3 C2H5 cis-4-tert.-butyl-cyclo-C6H11- 226. SO2CH3 C2H5 4-tert.-butyl-C6H4- 227. SOCH3 C2H5 4-tert.-butyl-C6H4- 228. SOCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 229. SO2CH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 230. SO2CH3 C2H5 4-F3CO-C6H4-CH2-CH2- 231. SOCH3 C2H5 4-F3CO-C6H4-CH2-CH2- 232. H C2H5 4-tert.-butyl-C6H4-CH(CH3)- 233. H CH3 (R)-2-H3C-O-C6H4-CH(CH3)- 234. H C2H5 (R)-2-H3C-O-C6H4-CH(CH3)- 235. H CH3 (R)-2,4-Cl2-C6H3-CH(CH3)- 236. H C2H5 (R)-2,4-Cl2-C6H3-CH(CH3)- 237. H C2H5 2-F-C6H4-CH(CH3)- 238. H CH3 2-Cl-6-F-C6H3-CH(CH3)- 239. H C2H5 2-Cl-6-F-C6H3-CH(CH3)- 240. H CH3 2-F-C6H4-CH(CH3)- 241. H CH3 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- 242. H C2H5 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- 243. H CH3 (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- 244. H C2H5 (2,5,5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- 245. H CH3 2,4-F2-C6H3-CH(CH3)- 246. H C2H5 2,4-F2-C6H3-CH(CH3)- 247. H CH3 4-Cl-2-F-C6H3-CH(CH3)- 248. H C2H5 4-Cl-2-F-C6H3-CH(CH3)- 249. OCH3 C2H5 (S)-4-F-C6H4-CH(CH3)- 250. OCH3 C2H5 (S)-4-Cl-C6H4-CH(CH3)- 251. OCH3 C2H5 (S)-4-Br-C6H4-CH(CH3)- 252. a C2H5 cis-4-tert.-butyl-cyclo-C6H11- 253. b C2H5 cis-4-tert.-butyl-cyclo-C6H11- 254. c C2H5 cis-4-tert.-butyl-cyclo-C6H11- 255. d C2H5 cis-4-tert.-butyl-cyclo-C6H11- 256. e C2H5 cis-4-tert.-butyl-cyclo-C6H11- 257. f C2H5 cis-4-tert.-butyl-cyclo-C6H11- 258. g C2H5 cis-4-tert.-butyl-cyclo-C6H11- 259. h C2H5 cis-4-tert.-butyl-cyclo-C6H11- 260. i C2H5 cis-4-tert.-butyl-cyclo-C6H11- 261. CN C2H5 cis-4-tert.-butyl-cyclo-C6H11- 262. OCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 263. OH C2H5 4-cis-(butan-2-yl)cyclohexyl- 264. k C2H5 4-cis-(butan-2-yl)cyclohexyl- 265. H CH3 4-F2HCO-C6H4-CH(CH3)- 266. H C2H5 4-F2HCO-C6H4-CH(CH3)- 267. H CH3 4-F2HC-CF2O-C6H4-CH(CH3)- 268. H C2H5 4-F2HC-CF2O-C6H4-CH(CH3)- - An agricultural composition comprising such an amount of at least one compound of formula I' or an agriculturally useful salt of I' as defined in claim 17 and at least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50228103P | 2003-09-12 | 2003-09-12 | |
PCT/EP2004/010132 WO2005025315A1 (en) | 2003-09-12 | 2004-09-10 | 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1662877A1 EP1662877A1 (en) | 2006-06-07 |
EP1662877B1 true EP1662877B1 (en) | 2014-12-17 |
Family
ID=34312369
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04765059.3A Active EP1662877B1 (en) | 2003-09-12 | 2004-09-10 | 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests |
Country Status (24)
Country | Link |
---|---|
US (1) | US8664235B2 (en) |
EP (1) | EP1662877B1 (en) |
JP (1) | JP4520989B2 (en) |
KR (1) | KR101141562B1 (en) |
CN (1) | CN100567297C (en) |
AP (1) | AP2006003539A0 (en) |
AR (1) | AR045743A1 (en) |
AU (1) | AU2004271715B2 (en) |
BR (1) | BRPI0414257B8 (en) |
CA (1) | CA2538242A1 (en) |
CO (1) | CO5650200A2 (en) |
CR (1) | CR8262A (en) |
EA (1) | EA010091B1 (en) |
EC (1) | ECSP066389A (en) |
ES (1) | ES2528250T3 (en) |
IL (1) | IL174196A0 (en) |
MA (1) | MA28019A1 (en) |
MX (1) | MXPA06002237A (en) |
PE (1) | PE20050510A1 (en) |
TW (1) | TW200526666A (en) |
UA (1) | UA81976C2 (en) |
UY (1) | UY28506A1 (en) |
WO (1) | WO2005025315A1 (en) |
ZA (1) | ZA200602965B (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005028438A1 (en) * | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivative |
CA2710171C (en) * | 2007-12-21 | 2016-02-02 | Merial Limited | The use of 6-halogeno-[1,2,4]-triazolo-[1,5-a]-pyrimidine compounds for combating pests in and on animals |
JP2010065024A (en) * | 2008-08-14 | 2010-03-25 | Ishihara Sangyo Kaisha Ltd | Pest control agent containing triazolopyrimidine derivative or salt thereof |
PL2369935T3 (en) | 2008-12-26 | 2017-04-28 | Dow Agrosciences, Llc | Stable insecticide compositions and methods for producing same |
TW201029575A (en) * | 2009-01-29 | 2010-08-16 | Ishihara Sangyo Kaisha | Triazolopyrimidine derivative or its salt, process for producing the same and pesticide containing the same |
KR102006039B1 (en) * | 2011-10-26 | 2019-07-31 | 다우 아그로사이언시즈 엘엘씨 | Pesticidal compositions and processes related thereto |
IN2014DN10675A (en) * | 2012-06-30 | 2015-08-28 | Dow Agrosciences Llc | |
MX358025B (en) | 2012-11-20 | 2018-08-02 | Glaxosmithkline Llc Star | Novel compounds. |
WO2017000277A1 (en) * | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
US10618882B2 (en) | 2015-07-28 | 2020-04-14 | Nippon Soda Co., Ltd. | Pyridine-2-yl pyridinium compound and method of using same |
GB201518456D0 (en) * | 2015-10-19 | 2015-12-02 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory, autoimmune and/or proliferative diseases |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE99794C (en) | ||||
DE55956C (en) | CH. GROOMBRIDGE und W. A. SOUTH in London, 40 New Bond Street | Brake crank for horse-drawn tram and other wagons | ||
DD55956A (en) * | ||||
DE1620694C3 (en) | 1966-10-03 | 1982-04-15 | VEB Deutsches Hydrierwerk Rodleben, DDR 4501 Rodleben | Process for the preparation of 5-methyl-7-diethylamino-s-triazolo [1,5-a] pyrimidine and its salts with acids |
FR1567021A (en) | 1967-01-27 | 1969-05-16 | ||
NL7712098A (en) * | 1976-11-10 | 1978-05-12 | Ciba Geigy | PROCESS FOR THE PREPARATION OF PHOSPHORIC ACID DERIVATIVES AND THEIR USE AS PLANT PROTECTION PRODUCTS. |
TW224044B (en) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
DE19629144A1 (en) * | 1996-07-19 | 1998-01-22 | Bayer Ag | Substituted triazoloazine sulfonamides |
DE10063115A1 (en) | 2000-12-18 | 2002-06-27 | Bayer Ag | triazolopyrimidines |
DE10121102A1 (en) * | 2001-04-27 | 2002-11-07 | Bayer Ag | triazolopyrimidines |
DE10121162A1 (en) * | 2001-04-30 | 2002-10-31 | Bayer Ag | triazolopyrimidines |
GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
-
2004
- 2004-09-09 UY UY28506A patent/UY28506A1/en unknown
- 2004-09-10 WO PCT/EP2004/010132 patent/WO2005025315A1/en active Application Filing
- 2004-09-10 PE PE2004000881A patent/PE20050510A1/en not_active Application Discontinuation
- 2004-09-10 JP JP2006525775A patent/JP4520989B2/en not_active Expired - Fee Related
- 2004-09-10 AU AU2004271715A patent/AU2004271715B2/en not_active Expired - Fee Related
- 2004-09-10 EA EA200600492A patent/EA010091B1/en not_active IP Right Cessation
- 2004-09-10 EP EP04765059.3A patent/EP1662877B1/en active Active
- 2004-09-10 MX MXPA06002237A patent/MXPA06002237A/en active IP Right Grant
- 2004-09-10 AP AP2006003539A patent/AP2006003539A0/en unknown
- 2004-09-10 KR KR1020067005022A patent/KR101141562B1/en active IP Right Grant
- 2004-09-10 CN CNB200480026209XA patent/CN100567297C/en active Active
- 2004-09-10 ES ES04765059.3T patent/ES2528250T3/en active Active
- 2004-09-10 BR BRPI0414257A patent/BRPI0414257B8/en active Search and Examination
- 2004-09-10 AR ARP040103254A patent/AR045743A1/en unknown
- 2004-09-10 TW TW093127554A patent/TW200526666A/en unknown
- 2004-09-10 CA CA002538242A patent/CA2538242A1/en not_active Abandoned
- 2004-09-10 US US10/570,854 patent/US8664235B2/en active Active
- 2004-10-09 UA UAA200603895A patent/UA81976C2/en unknown
-
2006
- 2006-02-22 EC EC2006006389A patent/ECSP066389A/en unknown
- 2006-03-01 CR CR8262A patent/CR8262A/en not_active Application Discontinuation
- 2006-03-02 MA MA28849A patent/MA28019A1/en unknown
- 2006-03-09 IL IL174196A patent/IL174196A0/en unknown
- 2006-03-10 CO CO06024511A patent/CO5650200A2/en not_active Application Discontinuation
- 2006-04-10 ZA ZA200602965A patent/ZA200602965B/en unknown
Also Published As
Publication number | Publication date |
---|---|
BRPI0414257B8 (en) | 2022-07-05 |
KR20060123095A (en) | 2006-12-01 |
JP4520989B2 (en) | 2010-08-11 |
US20060264446A1 (en) | 2006-11-23 |
ZA200602965B (en) | 2007-07-25 |
EA010091B1 (en) | 2008-06-30 |
US8664235B2 (en) | 2014-03-04 |
BRPI0414257B1 (en) | 2014-07-15 |
BRPI0414257A (en) | 2006-11-07 |
IL174196A0 (en) | 2006-08-01 |
CO5650200A2 (en) | 2006-06-30 |
AU2004271715B2 (en) | 2010-08-26 |
EP1662877A1 (en) | 2006-06-07 |
KR101141562B1 (en) | 2012-05-22 |
AR045743A1 (en) | 2005-11-09 |
UA81976C2 (en) | 2008-02-25 |
ECSP066389A (en) | 2006-10-31 |
EA200600492A1 (en) | 2006-08-25 |
JP2007505077A (en) | 2007-03-08 |
AP2006003539A0 (en) | 2006-04-30 |
CR8262A (en) | 2006-07-14 |
MXPA06002237A (en) | 2006-06-20 |
AU2004271715A1 (en) | 2005-03-24 |
CA2538242A1 (en) | 2005-03-24 |
CN1849070A (en) | 2006-10-18 |
WO2005025315A1 (en) | 2005-03-24 |
CN100567297C (en) | 2009-12-09 |
ES2528250T3 (en) | 2015-02-05 |
PE20050510A1 (en) | 2005-07-19 |
TW200526666A (en) | 2005-08-16 |
UY28506A1 (en) | 2005-04-29 |
MA28019A1 (en) | 2006-07-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1713786B1 (en) | 1-(azolin-2-yl) amino-1,2-diphenylethane compounds for combatting insects, arachnids and nematodes | |
EP1860941B1 (en) | Biphenyl-n-(4-pyridyl) methylsufonamides | |
CA2280270C (en) | Acrylonitrile compounds, process for their production and pesticides containing them | |
US20060069083A1 (en) | Pesticidal dibenzo(hetero)azepine derivatives | |
CN104169278A (en) | Isothiazoline compounds for combating invertebrate pests | |
EP1662877B1 (en) | 6-halogeno-[1,2,4]triazolo[1,5-a]pyrimidines for combating animal pests | |
US20080300280A1 (en) | Cyanobenzene Compounds for Combating Animal Pests | |
EP2069306B1 (en) | Quinolinylmethyl compounds | |
US20100010058A1 (en) | Azoline Compounds for Combating Arthropod Pests | |
TW200909421A (en) | 1-(azolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests | |
US20090136551A1 (en) | Substituted Dicyanoalkanes For Combating Animal Pests | |
US20080064730A1 (en) | Azine Compounds for Combating Animal Pests | |
CN101677552A (en) | The Aminoazoline and the urea derivative of control animal pest |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20060412 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL HR LT LV MK |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: BASF SE |
|
RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: MERIAL LTD. |
|
17Q | First examination report despatched |
Effective date: 20111118 |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20140704 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: SCHMIDT, THOMAS Inventor name: SCHIEWECK, FRANK Inventor name: OLOUMI-SADEGHI, HASSAN Inventor name: COTTER, HENRY, VAN, TUYL Inventor name: HOFMANN, MICHAEL Inventor name: RACK, MICHAEL Inventor name: PUHL, MICHAEL Inventor name: BAUMANN, ERNST Inventor name: VON DEYN, WOLFGANG Inventor name: GOETZ, NORBERT Inventor name: BUCCI, TONI Inventor name: KORDES, MARKUS Inventor name: CULBERTSON, DEBORAH, L. Inventor name: GROTE, THOMAS |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL HR LT LV MK |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R081 Ref document number: 602004046348 Country of ref document: DE Owner name: MERIAL, INC., DULUTH, US Free format text: FORMER OWNER: BASF AG, 67063 LUDWIGSHAFEN, DE |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 701213 Country of ref document: AT Kind code of ref document: T Effective date: 20150115 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602004046348 Country of ref document: DE Effective date: 20150129 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2528250 Country of ref document: ES Kind code of ref document: T3 Effective date: 20150205 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG9D |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150318 Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 701213 Country of ref document: AT Kind code of ref document: T Effective date: 20141217 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150417 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 12 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602004046348 Country of ref document: DE |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
26N | No opposition filed |
Effective date: 20150918 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: LU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150910 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150910 Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150930 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150930 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 13 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R081 Ref document number: 602004046348 Country of ref document: DE Owner name: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC., D, US Free format text: FORMER OWNER: MERIAL LTD., DULUTH, GA., US Ref country code: DE Ref legal event code: R082 Ref document number: 602004046348 Country of ref document: DE Representative=s name: VOSSIUS & PARTNER PATENTANWAELTE RECHTSANWAELT, DE Ref country code: DE Ref legal event code: R081 Ref document number: 602004046348 Country of ref document: DE Owner name: MERIAL, INC., DULUTH, US Free format text: FORMER OWNER: MERIAL LTD., DULUTH, GA., US |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: TP Owner name: MERIAL INC, US Effective date: 20170116 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E Free format text: REGISTERED BETWEEN 20170309 AND 20170315 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20040910 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: TR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141217 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 14 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 15 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R082 Ref document number: 602004046348 Country of ref document: DE Representative=s name: VOSSIUS & PARTNER PATENTANWAELTE RECHTSANWAELT, DE Ref country code: DE Ref legal event code: R081 Ref document number: 602004046348 Country of ref document: DE Owner name: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC., D, US Free format text: FORMER OWNER: MERIAL, INC., DULUTH, GA., US |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E Free format text: REGISTERED BETWEEN 20210211 AND 20210217 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20220920 Year of fee payment: 19 Ref country code: DE Payment date: 20220620 Year of fee payment: 19 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20220922 Year of fee payment: 19 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: IT Payment date: 20220926 Year of fee payment: 19 Ref country code: ES Payment date: 20221121 Year of fee payment: 19 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R119 Ref document number: 602004046348 Country of ref document: DE |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20230910 |